Beyond 9-to-5: Embracing the Fractional Work Revolution with Brett Trainor & Matthew Mottola

Brett Trainor (00:00.886)
Yeah, it's weird being on the receiving end of this driving end. All right, Brett, thank you for hopping on my man. Listen, you have an awesome podcast as well. This has been a blight. We've been able to meet only once and I'm super pumped to have a longer meeting with you. The podcast is our way to justify being able to steal people like yours time on our end is the way that I think about it. And you know, I'm

I'm just going to start off with a funny question, which is, someone like you, why in the world are you working fractional, loving the idea of fractional? Why? You could be making a lot of money as a VP somewhere else. Why in the world get into this thing called fractional? Yeah, I think it's an interesting question. And I was on that side for 30 years. I wasn't a VP for 30 years, but lived in that corporate world for a long time.

We may have chatted briefly in our last meeting that I actually went into management consulting for about a year and a half at the tail end of that. So probably not the wisest path to take, but hey, I thought I could change the world and we were ready to go. And I was just ready for a change. And quite honestly, I stumbled into Fractional by accident. I left consulting and I started a solo consulting practice. Doing that seemed natural. I figured out what the market...

that the company was charging my billable time at and I'm like, hmm, 50% of what I'm actually making. I'm like, I think I could give this a go on my own. So long story, a little bit shorter was I kind of stumbled into fractional leadership before I knew what it actually was, that there was a bunch of these small and mid-sized companies that were hungry for talent.

but didn't realize, I shouldn't say talent, but leadership and some experience that in the past they just couldn't hire because they couldn't afford to do it. And so it was kind of the perfect world. It gave me the flexibility. I've got kind of a short attention span. So if the fact I'm only working, you know, a day a week with the client on average, I can work with multiple clients and it just, yeah, it was a perfect path for me. I love it. So let's now do sort of the journey to here.

Brett Trainor (02:18.77)
And first, I know we skipped, right? So first off, where are you sitting? Where are you from? Where, let's start with that. From currently, I'm just outside Chicago. I kind of grew up in the suburbs of Chicago. And the life journey, right, if you will, I didn't even know. I was the first one in my family actually went to college. So I didn't even know what business was really when I started in.

You know, my wife cringes every time I say this, but my goal was, Hey, go to college and I'm going to be a game warden because I can be outside patrolling the lakes, you know, across the border. It sounded like a really good idea. Um, but then the reality set in after my first job and like, man, there's gotta be more to this than this. Right. It wasn't a game warden by the way, but working for a battery manufacturer and that kind of started my journey through.

through corporate America. So kind of eyes wide open or blinded, I don't know what the best way to think about that, but yeah, it's been an interesting journey for sure. And so for you listeners out there to listen for the Chicago accent, Brett, it's not a bad accent, but I can, little words, I'm like, oh, there it is, there it is, there it is, there's the Chicago. What, we're gonna kind of skip to the end, just in terms of how in the world do you live with the Chicago cold?

Starting to ask myself that now, we had a really nice summer. It was gorgeous. We didn't have, we only had, I think, a couple days over 100 degrees where the rest of the country was cooking. So it was absolutely beautiful. But yeah, the winters can be tough. We made a deal with my youngest is now a senior in college that we keep the house here in Chicago until she graduated college. So she always had a place to come home to. It was comfortable.

But you know what, she's less than 12 months away from that. So we'll see. We'll talk a lot about going warm or figure something out. Cause the beauty is you can work from anywhere. And so, um, the options will be open. We just haven't made a decision on where we're going yet. You're going to go Florida, Arizona, California. Where's, where are you thinking? My wife and, uh, her family, they're Floridians. And so it's probably predestined that it will end up down there. So.

Brett Trainor (04:37.27)
I like Arizona, Florida. I like Arizona. I like some of the other warmer, but yeah, it's one of these I'm not going to fight. So listen, so bring me into your world in terms of fractional. And I actually know, I think we skipped. Give us a background on what you do right now, Brett. We totally skipped that in the beginning. Yeah, no, not a problem. So if you check out my LinkedIn profile and the corporate escapee, I kind of...

stumbled into this when I knew I was done with corporate and I just needed to get out, but I didn't know what the hell I was going to do. I kind of talked about going to consulting, then fractional. Some of the other things I've actually figured out is you can make some money opportunistically leveraging your experience either through reseller or reselling services into your network. So it just became really opportunistic with where the opportunities lie.

So then I became on a mission of, man, I just didn't realize how unhappy I was in corporate until after I had left. And my wife, about a year after started my own thing, still, you know, growing pains, but she's like, man, what the hell was the matter with you? And she was referring back when I was in consulting still. And at the time, everything seemed fine, right? It was a good job. They absolutely paid you really well. You know,

kids, the family, everything was doing well, but obviously something was not right, right within me. And so that was the biggest thing is, man, if I was like that and I'm a pretty easygoing guy, there's got to be a hell of a lot more of me's out there, right in this, in the workforce that are, they're looking for something else. So I've made it my mission one to keep doing the fractional work, but how do I bring more people out of corporate with their experiences into this new

you know, future of work, which I'm sure we'll get into. But yeah, that's what drew me to you is what you guys were talking about and where the future is going. So like I said, one at a time, my mission is 10,000. I think I probably touched maybe a hundred. So I got some work to do, but we're getting there. I love it. So you represent, you know, okay, how I says five years ago, I wouldn't be running into people like you.

Brett Trainor (06:55.242)
And what I mean by that is that five years ago, there was incredible freelancers out there, but they were very specialized. They generally weren't coming from a place of leadership prior. And so they generally were ICs. They usually sat within something creative and marketing related or software development, but not the project management side, more so the actual execution. Now looking at you, MBA from Booth, right?

BS in economics from Iowa State, significant corporate experience. Five years ago, if I had told leaders that someone who literally looks just like you was freelancing or being fractional, we'd get laughed out of the building. But now, I got people like you, right, to stick on a slide deck and say, you need to access this person. And I'll give you a quick, you know, funny example only because I found this out this morning.

Have you, did you see what happened with Sam Altman over the weekend in OpenAI? Just at that headline level, he's out, he's back in, he's out, Microsoft hired him or something. So there's a great meme, okay, where basically it goes, you know, looking away like exactly, he's out, he might come back in, he's at Microsoft. But the reason that I think this is important for this conversation is that he, everyone would wanna hire him, right?

No one in the world would not want to have Sam Altman leading or in your company. Right. Mike, and usually hiring someone of high caliber is going to take what? Three plus months, six plus months if you can even get that person to come work with you. Microsoft hired him in days. And what we see from the freelance world is that you can have someone of high caliber within minutes depending on how you structured your program. And so kind of put it all together, Brett, and talking with someone like you.

The ability to have someone like you in my environment within days is massive, right? Absolutely massive and transformational. Now, help bring us into your world and help us understand what does the fractional environment look like? And that's, when we first talked, that was one of the things I was so excited to learn from you was literally just, oh, there's more people like you, right? Where are they? Where are they hanging out? Who are they? How many are they?

Brett Trainor (09:19.978)
And there's lots of data, right? Like there's a, I think it's like a 33% rise in a hunt and people making over a hundred thousand dollars freelancing, right? There's a 90% rise in people freelancing full time. But just, could you, could you bring us into your beautiful, beautiful landscape of Fractional? Yeah. And maybe in just a half a step back behind that, because as a deeper, I got into this world and you know, I leverage Mike podcast the same way you do to get to have conversations with a lot of really interesting people that probably wouldn't talk to me if I didn't.

it. That's here and there. I think that the subculture of the escapee world, I'm more, I still focus more on the broader like, hey, 20 years experience, Gen X leaving the corporate world, right? And what am I going to do? And I liken it back to our old high school days, right? We had the jocks, the brainiacs, the nerds, the burnouts, right? You name it and there was that. And what I'm finding under

that in the freelance world is you've got the fractional, you've got the consultants, the solo consulting shops. You've got the interims, which is not to be confused with the fractional's, interims is hired by a company for three, six, nine months to do a full-time job, right? Where they need a CFO that left, they need to plug somebody in as they look for the full-time hire. And not to mention the freelance and the projects and.

You know, the one-off, like I said, reseller agreements, right? That you can, you can build with it. And the fractional world, I think is a perfect, um, the backbone for what I'd say the future of work is because you've got to your point, a lot of experienced people that were not accessible to small and mid-sized companies and even some larger companies that, you know, can get tied down with, within hiring processes. And all of a sudden now, uh,

And there's a big fractional world, right? I actually spoke at, um, frac 2023, which was up in Minneapolis just about a month ago. Yeah. It was about a month ago. They had over 200 people at a live in-person conference, right. Set up, you know, fairly quickly. And, you know, John arms is leading that one. And then Kareen out of New York is leading another fractional community. She's got, I think now we're over 5,000 members, you know, so these are truly for paid fractionals working in companies. So it was a lot.

Brett Trainor (11:41.458)
more structured and larger than I thought it was when I first started doing it. Right. It just seemed like, ah, this is a good part-time gig, but no, it's there's, there's X, I don't want to call it industry standards, but it's starting to, to settle a little bit. And, you know, what was kind of missing from my side is the work that, that you're doing with John, right. That said, Hey, from the company side, Hey, there's a lot of really talented people out here and. You know, the, the one.

quote I love from a business owner was, hey, I'd rather pay, you know, for 50% of an A player's time than 100% of a B player. And what I think you're gonna start seeing with these fractionals is you can start building in a little bit of a team, right? So if you're a mid-sized company that really needs to refresh their sales and marketing strategy rather than bringing in a chief revenue officer, chief marketing officer full time.

And you can get three of those fractionals for the same price you would have of the full time hire. And you just got unbelievable amount of experience. And, you know, I think that the real value obviously is the cost savings. But what I've found is they don't bring me into the end of any of the junk, all the bad side of corporate. So I'm not in any unnecessary meetings. It's super focused on where the value is, where I can drive the most value. I think both sides get it.

Brett Trainor (13:06.198)
You know, how can I have, you know, one of my leaders only be part time. But when you think about all the work that your leaders actually do full time, you know, there's not that much difference when you're actually focused on what's driving the business forward. So, so I think while I'm starting to see it and definitely curious from your side to see these businesses starting to adopt, right. That these opportunities, I think the ones that do are going to move the ball much further, much quicker than some that are stuck in there.

their old ways. I'm not sure I answered the question coming out of that. No, you led the path to a better one. To summarize what you were saying is I think you pose an interesting thought and that thought is fractional, the backbone of the future of work. You started by sort of what the segmentation, right? We have freelance, we have fractional, we have interim. I mean, not to get too confusing, we have gig, we have contractor, we have

open, right? So many terms and I'm still trying to figure out like, what, what is the one defining difference between this all? And I think mine, the way that I kind of describe like what is different because there's an ex there's always been an external workforce, right? Tech has always been over half external forever. Most companies are over 30% external. But I think what's different about our worlds, I think

It's that you have a direct relationship with the person themself, not the agency or the whatever it is, the holding company above that. And I think when you have a either a marketplace or a freelance contract relationship, I think that's the only difference because freelancers can stay 10 plus years, we see there's actually higher retention of freelancers and there are full time employees. But so for you, like, what do you

What do you think is actually uniquely different if someone was to say, okay, I'm looking at a contractor or fractional. Is it the same thing? Should we just put it as the same thing? Is it different? Yeah. It's a good question. I think the where it would be, the difference that I would say is a lot of the freelance work, freelancers up in the past few years, which I 100% agree it's been more marketing focused, has been...

Brett Trainor (15:26.206)
more transactional, we're fractional, at least where the momentum and all the momentum is right now. They're actually a leadership position on your team, right? So it's more of a, it's even beyond a partnership. You're part of that organization now. And the way, you know, it's funny, I was just thinking about this over the weekend, the different relationships. So as an employee of a company, and not all employers are poorly run or managed, but I mean,

The vast majority, as an employee, they have control over you. They can dictate the time and what you're going to work on, where your priorities are. As a freelancer or a contractor, I think that's more of a transaction. Yes, I'm on my own and the transaction is I'm going to do this work and you're going to pay me to do this, which is, hey, nothing wrong with that. But then I think the third one, which is a true partnership becomes fractional. You're part of the team.

It's more of a, hey, it's we want the, you know, the, the cliche of the win win. But I think there's that that's where it starts. I think it's how the relationship is versus maybe what the title is. That makes sense. Yeah, there's a there's a leader named Adrian ton. He's a fractional CMO. And he's actually had a Singapore. And so the way he puts it is, I'm pretty sure he has like multiple

And we're going to get into like, what is a fractional pipeline look like? But so he's got multiple freelance client fractional clients and he'll do like Monday into that client's office. He'll be there all day. He'll do all his meetings and one-on-ones Tuesday in that client's office, do all those one-on-ones and he's guiding the strategy. And so as a, you know, fractional CMO, he's guiding what the plan should look like. What are the OKRs? How do we make sure we're on track or not on track? Typical green, red, yellow.

Right? Really, what does a leader do? They set the strategy and then they manage it from a green or yellow perspective. And if things go wrong, they take the responsibility. That's leadership. But so, uh, he's a really good case study. Maybe we'll talk about it later. So let's talk about for you, what are some of the cool fractional opportunities that you've done? I would love to love to love to hear like, what are the clients like? What was the work that got done? Where are some of the outcomes? I'm just, I'm so pumped to learn.

Brett Trainor (17:49.258)
Yeah. And I think it's funny that the hardcore fractionals may disagree a little bit with some of my definitions of it, but that's okay. I think my approach going into these clients is always more teach to fish, right? And I tend to focus more on the under 5 million in revenue. I think the sweet spot's probably up to 25 million in revenue where I would probably add the most value.

But the way I approach it, and again, by accident, this was kind of discovered through, you know, how this works. Because again, I didn't know what Fractional was, was helping kind of build out the infrastructure for these companies. Now, if you're moving into a larger company, then it's probably maybe you're going to tweak or rebuild. But a lot of these smaller companies, they may not have had a sales leader or a full-time marketing leader before.

So I viewed my role as, hey, how do we set up this infrastructure? Right. What's important? What is the, you know, the, the engagement model look like, you know, in some cases, they understand what sales and marketing actually are and how they work together. But a lot of the time there's, there's not a lot of processes in place. So how do we build that infrastructure and align that to where their goals are? And.

I think part two of what I've always looked for is, hey, let's get the infrastructure, but figure out what you really need. Do you need like a hardcore, do you need the branding person right now? Do you have enough awareness in the organization, of your organization? Or are we at the lead standpoint where now we gotta start developing some demand generation? And then once you develop it, who's gonna handle these leads? What's that process? So it's really just setting up the infrastructure. And then part two, helping them find my replacement.

right? Because one of the biggest things that I've found and where I'm spending actually more of my time now is helping these companies with, with these resources and right, it's getting more and more complex with who do I hire? They think, like I said, I think I need a full-time chief revenue officer and I'll actually, I would recommend you hire a director of marketing. That's got a good blend of brand and some demand generation with more of a junior salesperson that can follow up on the leads. And then over time,

Brett Trainor (20:02.53)
then we can start to figure out where you need to add the full-time employees. Adding to that level of complexity, one of the things that I've started to do is recommend a team into a specific organization, right? So this one company, hey, 3% of the market knows who we are. You know, it's a technology company, so we need to get the awareness out there. I think we focus, they only wanted to focus one product and hit or miss their entire number for the year.

And again, they didn't have some of the technology in place. So I said, let's get a fractional chief marketing officer and then look at a product marketer, right, to help. Because we need somebody that can own a product that's done it in a big company, that's kind of taken it from concept to say, all right, let's do all the work around this. You don't need the full company demand generation. You need this product because this is what's going to make or break your ear. So all of a sudden you bundle those two folks together with a CRM, you know, tactical person that can help build it.

You know what, they just spent less than, you know, $20,000 a month versus what they would have done on the hiring side. So I view my role more of, I like that a lot more than the actual fractional work because the fractional is good and it creates some flexibility in the way I do it. But ultimately I think there's a bigger fish for me to help fry. But.

I will

Brett Trainor (21:52.638)
what we were working on. And I think one of the things that business owners and or businesses should be aware of, at some point, it may run its course, right? I mean, the one thing I think my experience has given me in my younger days, I would have, I just rolled off of a fractional gig not too long ago. And it wasn't, I just wasn't the right resource for what they needed anymore. It needed to be more on the marketing and some of those other pieces.

that was better served. And so in my old days, I would have chased it. I'm like, I can do that. I absolutely can do that. But the value to being on the fractional side is we get to pick and choose the engagements that we want to be a part of that fits the best with what we like to do and how we want to spend our time. So that was helpful. No, no, it really highlights the opportunity cost. And I think one of the toughest parts of

and looking at like company adoption of this industry is that, you know, how do you tug on the heartstrings, right? Like if we're to say, hey, you can, you should buy this iPhone, right? We could talk about the technical specs and if you're saying, hey, we're going to buy this MacBook, we could talk about the M3 chip, the fact it's built in America. There's these things, but that doesn't get the heartstrings to pull, right? That doesn't get me to pay 3X for this iPhone as I would for an Android phone, which really makes no sense.

because the technical specs are the same, right? Like, but I buy the iPhone. And so when looking at our space, we have a similar problem where even though our metrics, looking at cost and speed and quality are 10X better. And so from a cost perspective, I mean, we can quantitatively prove there's 30 to 90% cost savings. We can quantitatively prove that we can hire someone in usually one to five days, but then there's like,

Okay, how do you get the person to move? Right? How do you tug the heartstring away from going with the agency they've always gone with or hire in full time? And part of what you just hit on is that opportunity cost and the fact that, you know, what if you don't go with a freelancer? Well, you're now stuck with a 300 plus a year expense if it's not the right fit.

Brett Trainor (24:12.558)
And you probably won't know it's not the right fit because when you are a full-time employee, you're incented to keep your job, right? You're paying kink for your kid's education. So whereas someone like you would say, listen, I love working with you, but you're better off having this person because not to get, you know, very, very selfishly, you want that person's referral. And so they're going to refer you if you treat them right. So if you say, hey, there's this marketing person that's a better fit, they're not going to go.

you know, F you Brett, you are terrible. They're going to go, Oh my god, Brett, you just, you just saved us so much money and gave, and you put us first, right? So, so selfishly, the incentives are aligned in a freelance economy in a way that is so much better for the client, but then also you. So what would you say, let's, let's try to hit the spike on the bad part about this. What is, and you could say there's none, but I doubt it. What are the bad things about?

the fractional economy. Yeah, I just want to tie off on what you said with the hard strings. I think the underappreciated, and you mentioned it was the risk, right? You can really minimize risk by going down a fractional path versus hiring somebody full-time. Because you're right, you're probably six months. It's an 18-month mistake, and depending on the size of your company, it could sink you, right? By the time you realize you made the mistake, you have to go higher. And I think the risk of not knowing what you need, right?

to your point, it could be, you know, three months to hire a certain position in a corporation. And is this even the right position that you need? So I think the speed, the risk and the expertise that you can pick up, just the expertise you need is so important. So I think that the downside I would say from, well, you want the downside from my perspective or from the company perspective? I want it from you.

I want it from you. To me, it's very clear when looking at why you would do this. I assume you make more money doing this just based off the data. You have control. You're able to say things like, maybe next year our family will move to Florida. And there's no hesitation in your voice. In talking with my old boss at a large company I worked with prior, she was like, we really want to move here, but is the company going to pull us back?

Brett Trainor (26:35.494)
Right. And so you just don't have that. So the benefits are very, very clear. But it's not all sunshine and rose. So what in your eyes, what are some of the bad things about this? Yeah, I think, I don't know if I go as far as bad, but the potential negatives, and I warn people go into this with eyes wide open, right? Because the paycheck and the benefits are consistent. Every month.

As long as you don't get laid off, you know what you're gonna get. And most people that floor, so I look at it that way, the floor is set in corporate. You're also capped, how much money you're gonna make unless you're in a sales position with unlimited quota or you can commission, you can hit, or management that's got huge bonus potential. You're basically, your finances are capped. But in your world, in the fractional world, you're only capped by one year, your time and your ability to reach more.

customers. So the upside is much greater than what it was. Because you can see, and I've seen and I know seven figure businesses that are one person businesses now, right? So it's definitely possible. And it's depending on how hard you want to work and back to that balance. But the downside is your floor is zero. Your floor isn't a paycheck anymore. And you have to be willing to take on some of that risk. Again, I call it risk only as hard as you're willing to work because the opportunities are there.

And there's just not a lot of people asking for these opportunities. So in the short term, it's a big win just by doing versus, you know, that old adage, you know, can or will. I was like, I could do fractional. I do have the experience. I can. Yeah, you can, but will you? And the people that are will-oos right now are the ones that are finding these opportunities. And most of it comes through your network.

I can give you one little hack that I found that that's actually worked well for fractional is when a company's got a job posting for a certain position that fits your background, I'll message or email the CEO of that company and say, hey, are you interested in doing this on a fractional or a part-time basis? Are you sold on making this a full-time equivalent? And shocking, you probably get 50% response. 50% of them are going to be dead set on doing a full-time.

Brett Trainor (28:57.67)
This is what they want to do. But again, we just laid out why they should consider a non full time option, right? The risk, the cost and all that, that good stuff. So I think that's the biggest risk is you got to, you know, you got to bet on yourself. I think the other thing that people under appreciate is how do I manage my time? It sounds silly.

But coming from corporate where probably 70 or 80% of every day is kind of set for you based on meetings or deliverables that you have to provide. All of a sudden you own the deliverables, you own the calendar, you own the schedule, you own the to-do list. And I found, you know, most people thrive in that, but there's people that that's just not comfortable. And so, and this would not be a good, good environment for them. You, so I'm putting a little, I'm putting a little sticking up.

So reaching out directly to the CEO of a job post and saying, hey, good role. Have you thought about fractional? You would say that's around a 50% hit rate of them being open to it? At least accepting the LinkedIn request and then 50% saying it's

curious, but most of them are full-time equivalent. And again, that was a small sample size. So I would love to do this at a much larger rate. It was just literally I had. So this was, I'll call this my phase when I was seriously looking at, what do I call myself from Fractional? Because I do more than just chief revenue officer. I like the idea of chief of staff, be helping CEOs manage their strategic priorities. But

that role is half defined as managing the CEO's calendar. So one I had to do was, this was a strategic position, not a administrative position. And just as I saw those jive, a LinkedIn job alert that anytime a CSO position popped up, that's what I was gonna do is see if I can connect with the CEO, if I connected with them, then I'd ask them if they were open to fraction. Like I said, that was a short sample size, but. Yeah.

Brett Trainor (31:07.83)
You know, it works. You know, the other, the other trick, um, as we're talking about just how to connect with people, this is my other LinkedIn hack. If you hear somebody on a podcast, I've got, I would say 98% success rate of connecting with guests on any podcast, just by saying, Hey, I heard you on a podcast, love the work that you did. Um, even if you're not asking for anymore, I very, very few don't, um,

except the request. And then if you try to engage, I would say probably 50% of them actually do actually engage at some point. So just a little side tip that, you know, it's worked well for me. It's kind of crazy against back to the doers and the non doers and just doing it sometimes is half the battle. It hits on it's funny. I can tell you're good at sales as part of it. You know, most

I mean, this is one of the creative tensions is that most good and this is, I wonder if we can ever get to a place, I hope we can as an industry, but you know who I actually most admire is the, what was Thomas Edison's company called again? Do you remember? It was, it was, so I mostly admire the engineers.

that have zero level of abstraction, zero level of politics, zero level of caring about climbing the ladder. All they care about is whatever technical challenge they're working on. I admire them so much, right? Like that is to me, I'm like, that is, boy do I admire them. Now, where I'm worried is that full-time work is actually pretty good for people like that.

right? They never have to worry about where's my next paycheck coming from. They never have to worry about healthcare, anything like that. All they have to worry about is that they're making progress in what they're working on. Right? I hope we can get to that point as a freelance economy. We're not, we're definitely not there, right? We're not even close. And it's, I don't know if we'll ever get there, but I hope we can. I hope, hope we can now let's get into where you think these fractional folks are getting worse.

Brett Trainor (33:26.666)
And the reason I ask, so in people listening to this podcast, there's three segments. There's corporate leaders that are scaling their freelance workforces. There's industry leaders, so these are the platform founders, these are the industry solutions. And then there's the people like you, which are the fractional folks themselves. Now the last two buckets, the folks leading platforms and the fractional individuals like you. They are always wondering.

where does the next or where should we be trying to fish? And there's massive creative tension in that our marketplace is the right place for me to fish. And what I always tell the individuals are the marketplaces are built just to find you work. And so if you don't like them, it's because they're not doing a good job at finding you work, not because the incentives aren't in the right place. But so where do you think fractional folks and not even where do you think, where are you seeing

Fractional folks finding work is it on marketplaces is it on LinkedIn? Where do they find a work? Yeah before I answer let me I just want to you know just briefly about what you said with the being able to focus Which historically I would agree but with you know layoffs and you know Forbes has got a layoff tracker now And I don't know when the last time you had to find a new job But you know one of the taglines I use it's easier to find your first customer than it is your next job, right?

These guys are sending out 200 applications a week, and maybe they interview four people and just trying to find what that full time. So whether you like the idea of selling or not, there's part of it that you're gonna have to be doing that. And I joke that sales finally caught up to me because I was never the used car, right? I take that, man. I'm a problem solver, this is the problem I solve. And if you have this problem, here's the cost to solve this problem. It's just a simple reframing.

But even I can get some of the introverts or the heads down, I don't want to sell type to think differently about it. And I think where the opportunity lies, yes marketplace, but marketplace can be competitive, right? What I've found in, let's call it the last, least friction or the path of least resistance is into these small and mid-sized companies. So the 2 million to 25 million in revenue, right? They have the problem. They've obviously got a...

Brett Trainor (35:50.894)
product that works because they've gotten over that, you know, the million dollar threshold, need help scaling it to that next level, but have no idea how to do it. And so as a fractional, me going into those types of companies or into those worlds or networking to say, hey, who's open to fractional type work is, you know, when I get that meeting with a CEO or whoever may be hiring within that world, you know, it's me against do nothing.

Hey, those are the two scenarios. Either they're going to hire me or they're going to do nothing because it's not like there's five or six other people they're looking at or thinking about bringing in. This is something that's new to them. And I'd like to take my chances every time with me selling do nothing, right? As those two options. I'm also seeing the, obviously the startup world, right? Can be fluid and the lack of money that's going in investments right now. But again, they have the same need for.

talent and they may not need full time at this point, but to get some experienced folks to do it. So I think those three and a surprising one, and I haven't actually tested this myself, but the consulting firms, both the boutique and the biggies are now looking and leveraging more and more the fractional or the freelancers right up to 20% of their workforces are now based on that. So that's why I encourage people that are not.

comfortable just networking and you know asking for business those types of things then you know, maybe as a subcontractor for other Type either platforms or businesses would make more sense because then you're not responsible for your own business development as much But you know and again, I think people like you I found you through your Forbes article right talking about the future I'm like, yes, somebody gets where we're going. So I think the more and more this opens up

It is going to create more of a, again, the marketplaces get competitive. I do think it's a great place to start to see what's out there, who's looking for your skills, but just a little extra effort, I think, can help you find specifically the roles you're looking for and avoid the competition of some of these other type of places. Yeah. And related to that, right? So we got about 10 minutes left.

Brett Trainor (38:14.334)
Related to the marketplaces, what are the three key activities that you think really move the needle for an individual? I don't want to use the word finding work, but I want to use having a healthy pipeline because I'll give you some data on...

Before Human Cloud, we built a venture-backed software company called Venturell, and it was focused on the individual freelancer. The biggest takeaway was that 98% of freelancers, they would bite when you said, find work, find work, find work. There was definitely this short-term mindset that drove me nuts because the reality is you're not a...

It's just like any business. It's not about finding work. It's about retaining and upselling and growing, right? So for you though, what are three things that any individual can do to really have a healthy pipeline? Yeah, I think the first one is one you have to be willing to network, right? And again, don't go out just give me, give me, give me, but is there something that I can do in return, right? Because...

Again, at least the folks I work with have 10, 20, 30 years of experience. They have some experience, but their networking in the past was probably more related to job searches or opportunities that may be coming up. Or if they're in sales, maybe it's, hey, how do I get into this type of company? But it's more just be curious when you're talking to folks. And then two, just mentioning, well, let me take a step back. The other thing is I'd be crystal clear.

about what you're focused on, right? Because I think one of the dangers for us or for me is I could do that, I could do that, I could do that. Well, if I'm meeting you, Matthew, for the first time and I tell you all those things I can do, you're gonna meet somebody two days from now and you're not gonna remember what I do because it was kind of a little bit of everything. There might be something of interest. So as you're getting started, pick one problem that you solve, one industry you wanna solve it for and come up with one offering that makes sense. So as you're meeting with folks,

Brett Trainor (40:28.298)
you can say, hey, Matthew, this is what I do. Here's the type of things I'm looking for. You come across anybody that's looking for this, please let me know. You're gonna remember me because, oh, that's the guy that does this, right? And I don't care what it is, if it's transactional or a doer or leader or whatever, it just...

Get the momentum and then once you have the momentum, then you can open it up, you can explore other paths and see what makes sense. So that's the biggest one is just get the momentum going. It may not be your most ideal client, it may not be the most ideal work you're doing, but all of a sudden you get one, then you get two, and then you can start to get pickier about what your next engagement looks like. I think too often, I think I actually posted something on LinkedIn this morning, depending on.

obviously when this goes out about, right, we get so hung up on the early days of the aesthetics and do I have the right website into my business cards and the right title? At the end of the day, I talk to people all the time when I network and I get, you know, they're looking for full-time, right? So I'm urging them to, as you're looking full-time, consider fractional and contract. And just by when you're networking with folks, hey, I'm also open to some fractional contractual work.

You know, the last two people I had conversations with actually got leads, you know, within two days because they just changed the conversation that they were having with, with folks. So right. Again, it's not rocket science. It's just, you know, be true to the problem that you solve, be focused on it. And then like I said, it's, it's easy to chase all the shiny objects. And I still do this all the time and I'm getting better at it, but, you know, it's, it's creating that focus and then kind of center off of.

where your expertise is. And like I said, there's plenty of other opportunities, but just get the momentum going. I love it. So I think the big takeaway too is just reduce it to one. And that has a lot of implications, whether it's for the individual or the marketplace, you name it. The last thing someone at our level wants is to hear a bunch of things, because we really only remember one. And I swear, Brett, the older and more experienced we get, the more we're just like,

Brett Trainor (42:41.226)
tension span gets tinier and tinier and tinier. Right? Like, I miss I miss when I'd be able to listen to someone talk and say like more than three things. But now, I'm like, Okay, what's the one thing I can take away? What's the one thing I can take away? And that's it. So listen, so last question for you. And and that is, to be honest, prep, I'm just going to give you two minutes. Whatever you think our listeners should hear.

I'm not even going to give you a question. I'm just going to give you an open prompt and maybe it's me being lazy. But I just think someone like you, for those listeners out there, the fact that someone like you is prioritizing this space is massive. The fact that someone like you is prioritizing a fractional journey over being a VP is such a loss.

for those that only prioritize having full-time leaders and such a win for those that can be creative and flexible. And so I just literally wanna give you two minutes. You can say, you know, where you hope the space goes, you can say the biggest challenge, literally over to you, Brett, two minutes. I'm just gonna sit back and not say anything. No, I love it. I appreciate that. Cause you know, I will get on my soapbox. First one is I think.

You're right from leadership, from a corporation standpoint, it's going to hit a crossroads here pretty quick because you've got, I joke about the boomers, but they're starting to retire age out. You've got Gen X, which 42 to 59, somewhere in that age group. We've grown up through three transformations within the B2B space, through technologies, et cetera, leading. If you get more people like me, and there are more and more people like me that are going to exit.

who's going to take over the leadership roles, right? That if you're only in the 30s, there's definitely some talented leaders in there, but just the gap that it's going to create from a leadership perspective is going to be huge. That's one from the corporate. And two, I think on a more macro level, this is absolutely the future of work in the sense that, you know, I spent a lot of time, you know, trying to go through digital transformation with B2B companies and say, look, man, if you were built before the year 2000, your company's not built to sell or engage with.

Brett Trainor (45:01.902)
customers today is just super siloed, operating budgets. If you're in corporate listening to this, you get it. Sales has got an operating budget, marketing's got one, technology's got one, and try to get everybody online to work on one thing. Yeah, forget about it. And so where I think the future, and you guys are kind of leading this, or reporting on it, or driving it, however you want to do it, is we're gonna move away from a hierarchy and move more into an ecosystem. And...

Businesses need certain specialties and I don't want to pay for all the other crap, right? I don't want to do overhead. I don't want to do benefits. I don't want to do all these things. I need somebody that's really good at HubSpot X, Y, and Z, right? And maybe need it for six months, 12 months, whatever it is. But all of a sudden you've got an ecosystem of specialists that you need specifically for your business in order to drive it. And I just don't think the world is necessarily set up. The corporate world is not set up for it.

right? I think the small and mid-sized companies where I really had this, this aha moment was working with, you know, seven figure companies, individuals, right? Million dollars, one person. Then I work with, you know, a small business that's at two and a half, three million in revenue. You got 22 employees. I'm like, what, what do you need 22 employees for? It's just the inefficiencies are unbelievable. And so how do we build the right grow, you know, scalable?

organization of the future, it isn't going to be all full-time equivalents. Now there's dangers with all of it. And, you know, I've lived in the corporate world where it's really hard to manage full-time equivalents, let alone what you're trying to do and manage, right, a freelance economy. But if you pull it off, man, the benefits, the margins are so much better that the outputs are better. So that's my macro soap boxes. We're heading this way. And the, the analogy I share with, with folks.

is like a movie production, right? So you want to build the next blockbuster movie. You got hair, makeup, script, everybody's all their own independent companies that come together to work on this thing for 12 to 18 months, release it. They all go their own ways and some will come back and work again. And the other one, if that doesn't resonate is like Ocean's Eleven, right? If you recall that movie where they're gonna rob the bank and guess what? Danny needed it.

Brett Trainor (47:19.742)
safe guy, he needed a costume guy, he needed these things, they all come together for the greater output. And then they went back and did their own things. So to me, it just seems natural that that's where we're gonna head back to and the companies that embrace this. If you're a big company and figure this out, kudos, because you're gonna save not on time, but push forward in the direction. If you're a mid-sized company that figures this out, you can really drive your business forward. Yeah, I love it. It may have been more than two minutes, but I'm close.

You deserve the extra minute and a half, right? Especially just the aspect of a...

your senior leadership is going to be leaving, do you want to fall off a cliff or do you want to retain the knowledge and retain the training? It's such a crazy like, I remember when I left Microsoft, I would have totally worked 10 hours a week, right? It did not have to be a binary solution of FTE or nothing. I would have totally done 20 hours a week, 10 hours a week, worked in a fractional basis and they would have been much better suited because the reality is...

the last whatever it was four weeks that I said, okay, we're gonna D, you know, D, D on forever is called. I mean, there was so much knowledge lost that I would have been more than happy to keep going. So it's that you know, that's an angle of, yeah, you're gonna lose your senior leadership. And do you want to fall off a cliff? Or do you want to keep going? I love it. So listen, you got two questions, you got fun questions, you pick which one you want to answer first. First one is going to be favorite book. Second one is going to be favorite animal and why.

favorite book. The one thing I've done since I started this podcast was I probably had 50 different authors on it now, so I've got a ton. I think for the business that we're in right now, Who Not How is probably my go-to book. It's Dan Sullivan and Hardy. They talk about the problems that we face. We get too hung up on how.

Brett Trainor (49:19.49)
But the better question is who. You get the right who's in, then you don't have to, I mean, it sounds like a Dr. Seuss after a while, but get the right who's in, they'll figure out how to do it better than you will. And to me, it just makes sense. And the tag on book that they wrote is 10X is easier than 2X. So as you're trying to grow your business, you think differently. And that's what he challenges you do. It's either to go 10X and 2X, because 2X is basically just doubling the effort. With 10X, it makes you reconsider the way you do it. And I probably have other.

and other books that I could add to it, but that was those two I think from this podcast makes the most sense. And I'm sorry, what was the second question? Favorite animal and why? Favorite animal. I don't know, the dolphin always appealed to me. They're pretty smart, but they're playful, right? They don't seem to have a care in the world as they're floating around in the water out there, but they still get shit done.

You know, the first one up before you said dog. I think like 60% of people say dog. I totally would say dog. But dolphin is, it's unique, Brett. It's unique. Well, listen. You think they look carefree as they're just floating around in the ocean? Oh yeah. Oh, and they're extremely smart. Yeah, and they're extremely smart. No, I hear you. So listen, Brett, where can our listeners find you? I think the best way is LinkedIn.

That's the core of my business. That's where I handle most of the interactions. Or you can go to bretttrainer.com. There's three T's in the middle there. And it's got more information. Yeah, happy to connect with anybody that has questions. Like I said, I'm open to the network. And like I said, I'm not shy about sharing opinions. So happy to connect. I love it. Brett, thank you so much for hopping on. Matt, thank you for having me. I really appreciate it. It was a great conversation. Hey, by the way, Matthew.