The curse of the video freelancer, and... how to break it - with Grant Jamison. EP #284
8 Dec 2025 · 27 min
Podcast interview (Den Lennie with guest Grant Jamieson) about Grant's journey from freelance videographer to running a small video production company (Lift Video). Topics include the freelancer ‘feast-or-famine’ problem, hiring subcontractors, mindset and self-doubt when shifting from founder-as-operator to founder-as-owner, an initial niche in manufacturing/transport that didn’t scale, a pivot into healthcare/aged-care work that proved more receptive, and using LinkedIn (posting + connecting) to generate leads. Grant describes practical steps (hiring editors/shooters, planning the year, profile/copy changes on LinkedIn) and emphasizes persistence and habit-building in outreach.
Questions this episode answers
October 10, 2022
EP #284
Start of 2022 (January 2022) — Grant says he started Lift two years ago and that it began at the start of 2022.
Chapters
G', day, guys. It's Dan here from the how to Scale a Video Business Podcast. And this week, I have got one of my clients, Grant Jamieson, on the show. Now, Grant's been a longtime listener of the show, and we've been working together for a couple of years now. And today, Grant's going to share his journey from being a freelance videographer to some of the journey he went on to become a proper video production company, one that employs people that doesn't have him being on the tools. And the reason I wanted to get Grant on the show show was I wanted him to share his journey and the mindset journey he's been on and is still on in helping you realize that business is a journey, that there's a long way to go. You know, you never really feel like you're done, but I'm certain that you're going to find this to be very valuable because Grant's just a young guy who's just achieving an awful lot in his business. But what I love about this interview is he's very open about the challenges he still has. So I think you're really going to enjoy this. Please do like and subscribe and enjoy this interview.
G', day, Grant. I'm really excited to finally get you on the podcast because the journey you've been on, I think is going to be really insightful for other videographers who are perhaps frustrated with what they're doing and want. Want to do more. So, first of all, welcome to the show. Thank you for. For spending some time with us today.
G', day, Jen. Thank you for having me. Long time listener, first time caller.
I know.
No, I've listened to this podcast for so long, so it's a little bit exciting to be here finally.
Well, I mean, I wanted to get you on because.
I'm really proud of the journey you've been on. You are an inspiring young man who is, I think, really pushing the boundaries of what is possible for a videographer who wants to transition away from just being a freelance videographer into being a business owner. So I suppose for the sake of logic, why don't you start at the beginning and tell me, you know, your story, how you got to where you are today.
Yeah. Cool. So basically, I was working as a production assistant at a production company in Melbourne when I left high school. So I was there for six years, got made redundant, which was cool. You know, I'd learned a lot, so that was. That was fine. And then I got a corporate job as a videographer, and I Lasted about four months.
It was not for me.
And as in, like, employed in the company as the videographer in house.
Yeah, yeah, yeah. So massive corporate global organization.
And, yeah, at the time probably just wasn't the right fit. And then I decided to go freelance. And that was four or five years ago. So I've been doing that ever since.
So when I met you a couple of years ago now.
You were Grant Jamison Videography, and you had some cool clients. But what were some of the challenges you were experiencing as Grant Jamison Videography?
Oh, where to start? So many challenges, really. So, I mean, the main thing was I was just spending so much time shooting and editing. I'd get a huge glut of work come in and then nothing. Like, I'd finish that. I'd work crazy hours to get a job done and then I'd have like a week of like, oh, I don't have any work, so better call up a few people, send out some emails. And it's just like that roller coaster again and again and again and again. So that was kind of the biggest challenge.
And so when we first met, you were, I think, running a pretty, pretty successful freelance video business. But as you mentioned, it was just you. So you were making okay money, but you were doing all the work and you had that kind of feast and famine, that kind of roller coaster. Everyone, I'm sure who's watching or listening to this is very familiar with. So what was it that made you want to change? What was it that made you want to kind of like break away from that? What was the big sort of pain points?
To be honest.
I loved working with my clients and helping them in their positions and kind of guiding them and educating them on what can work with something I'm good at, which is making videos. But I was really tired of editing, especially like I'd been doing. I've just been doing it for so long, I just was pretty over it. So that was probably the main thing that made me want to transition into more of a business owner role rather than a freelancer. Yeah, I'd say definitely trying to just get rid of the editing. And that means I can focus on doing more of the stuff I love, which is working one on one with my clients, producing. And I still do a little bit of shooting, although I'm trying to move away from that a bit now as well.
So tell me, tell me about that journey. So you realize that you want to do less editing, you want to turn your company into business. But one of the things that There seems to be a lack of. Or certainly from my perspective, what I saw as a gap was there's an endless supply of videos on how to edit, how to grade content, on how to.
Shoot light. But where did you go to start figuring out how to turn your freelance videography business into something that was bigger than you, that it's more of a proper business? What kind of things were you doing to try and figure that out?
Yeah, well, look, I. Swell. Before denleny.com that is. Hadn't heard of it just yet.
So, yeah, I think I'm curious because it is. I think this is a problem that a lot of people suffer from is where do you get that kind of information from?
Yeah, look, I think you sort of start reading general business books like the classics like E. Myth Revisited, and. But still, the concepts are still a little bit outside of what I can kind of grasp. But at the time, I remember trying to read these business books, but still not quite getting it. And you're right, there's so much content out there on the best cameras and the best editing, but your clients don't really care about any of that crap. So it really took me a while to figure out, right. I need someone who can kind of show me the business side of things. I need to change that mindset away, to move away from focusing on gear and worrying about that kind of thing and focusing more on working on the business. And that's when I started listening to your podcast. So that was definitely a starting point. And then in combination with other mentors as well. So it's kind of just was finding a few mentors who had already done. Had already done it basically, and were already running their own video business. And I could kind of learn a lot and ask questions. And slowly I realized that, hey, I have to change how I think about it and I can't be constantly working in the business. I've really got to spend a lot more time working on the business and reaching out. And yeah, that's. That's kind of the gist.
It's funny, isn't it? Because, I mean, we've all read the E. Myth and that that's a very common book that I think we can relate to, but there's still a huge gap between understanding what you should be doing and actually doing it. So talk to me about that journey because I know that, you know, we've worked together quite closely on the evolution of Grant Jamieson videography to lift Video now and talk. Talk me through the steps that you went through and Maybe some would be like, be. Feel free to be really honest about the resistance you felt in some of those processes because I know we've had numerous conversations about that journey.
Yeah. So I mean, as in transitioning across. Yeah, yeah. I mean, it's just taken a long time and to be honest, it's still a journey for me. Still trying to make sure that I'm doing the right kind of work and not stressing too much about going on shoots or getting into the edit.
In terms of steps that I took. Oh, it's just been like so, so slow and there's been so many that I don't know where to start. But I guess the biggest thing was starting to hire subcontractors was probably where I started. So I was Grant Jamison Videography and then I was like, oh, maybe I'll just try it. And I had a few editors just helping me out here and there and then. But I was still doing a lot of the editing as well. Like they do the bulk of it and then I jump in and finish it off. But then once I started the vba, I started to realize there's probably a better way of doing it and trying to think more strategically. So planning the year out in advance and trying to hit, you know, strategic goals rather than just being busy for the sake of being busy.
And what were the. Some of the kind of. I suppose probably the best word to use is emotional challenges. Like, you know, when, when we're changing the way we operate. Probably a mindset is a better phrase. What were some of the mindset challenges you experienced when making that transition from you being kind of your name above the door to turning that into a kind of brand. What were some of the challenges you experienced during that process?
Yeah, like a lot of like self doubt in particular. Lee. So just wondering if I'm doing the right thing. And you know, you get.
Friends and family who kind of, you know, say just like, you know, not in a meaningful way, like not in a mean way, but just comments like, you know, are you sure you want to keep doing this? Are people still paying for video? And that kind of adds to the self doubt as well. Even though it's coming from a place of care, you know, there's. It's kind of a struggle to work through that and I guess build some confidence and belief in yourself, which took me quite a while to do it actually took me a while to get the confidence and get some self belief to go from Grant J Videography, where I was doing it all myself and transition into more of a brand where I can kind of step back off the tools and trust, like my new videographer and trust my contractors and also educate my clients. And so that they now know that I'm not necessarily going to be the one that rocks up and shoots and edits.
And that's something I think a lot of videographers really struggle with. They're like, oh, but the clients want me, and if I don't show up, somehow the deliverable quality will go down. So you changed your business. You came up with Lyft Video.
How did you transition your clients into that new way of working? And did you experience any resistance, or was it all in your head?
A lot of it was in my head. At the end of the day, they don't really care as long as the product looks good and says what it does, what you said it was going to do, there was still a bit of just educating. And the way I would do it is kind of in a jokey way. I'd be like, look, to be honest, this guy's better than me. You're going to love him. I've gotten a bit rusty anyway, so it's kind of that jokey. You don't have to worry about. And the first kind of few shoots with one or two clients, I still came on the set with a producer, like, as a producer role, and I kind of let them see that our shooter videographer was. Was crushing it. So. And he. He probably is better than me, but, you know, don't tell him that.
Well, that's. But that's why we hire people, right? We want to hire people that are better than us. And I love the fact that you kind of used a bit of humor to transition the clients, but also you held their hands on the first couple of shoots, but then once they got felt safe, you didn't need to be there anymore. Which. Which is amazing because that's really, you know, a business that relies on you to be at every point of the conversation is. Is not a business. It's a really badly paid job with a terrible boss. Because you're. You're kind of having to do everything.
Yeah. And I always joke, my boss is an. So sorry, you might have to cut that. I don't know.
That's cool.
We're.
We're completely. Never gives me time on this channel. Never gives you time off. The pay is crap.
Yeah, yeah. Anyway.
And you're always the last to be paid.
Yeah, yeah. Yes.
But. But now that you've been. How long have you been lift Video now.
So two years. So I started right at the start of COVID which was perfect timing. Yeah, could not have time that better. But yeah, we started lyft start of 2022, I think it was January.
And tell me about, you know, how Lyft came about and what, what the original focus of Lyft was. Because I think that's an interesting story as well.
Yeah, it is, it's pretty interesting. So essentially we went down the path of niching in a space like an industry specific kind of niche and we chose manufacturing and transport. And the reason I chose that was at the time I'd done a little bit of research, probably not enough, probably not enough testing in retrospect. And I thought, yep, this is great, let's give it a go. So we went with Lyft video production, kind of like a forklift, I guess, kind of name. Like it kind of felt like it worked in the industrial space because that's kind of who we wanted to work with and do more work with. And that's where the name came. And then over two years started to realize that the niche wasn't really working that well.
So yeah, that was a challenge.
And what was some of the specific. Because I think this is really interesting that, you know, part of the reason for a backstory you chose this niche was you had a couple of fairly big clients in the manufacturing transport logistics space. And so it seemed to make a lot of sense to keep going down that route. But you discovered a particular challenge, didn't you, with the manufacturing space.
So the manufacturing space didn't really have any marketing per se, like they had a little bit. But I found it really hard to go in and I guess sell them on a video or see how video could help them when they didn't even have a marketing manager or they didn't have any marketing at all. So that was the manufacturing challenge. And there were still a few manufacturers that were pretty open to it. But yeah, that was the big challenge there. And then transport, I found that they just didn't really like me working with their competitors, which is kind of odd, like I would have thought. I guess my expectation was they would have, it wouldn't have bothered them because it'd be like, yeah, that's just lift video. They're experts, they do heaps of like transport kind of video and that kind of thing. But no, that was not the case.
So that, that presented quite a unique challenge. And I know that a few months back we had a bit of a one to one and you were Quite frustrated that you'd spent a long time going down, probably a year, going down this path, very much with a focus on the marketing. And then you realized that it wasn't working. And I feel that what's important to share here and what's really cool about you coming to do this is that business is really hard. And sometimes you have to go down a pathway and it's the wrong pathway to realize it's the wrong pathway. But when you get down that rabbit hole, you can feel like you've just wasted your time. But what was interesting is during your marketing of Lyft, another opportunity came across, your path, which was completely outside of your niche. Tell me about that.
Yeah, so basically there was a project that came about in the healthcare space, and it was a pretty large project filming a bunch of aged care homes. And, yeah, completely different to, like, transport trucks and like, manufacturing engineering. And then suddenly we were going in and filming, you know, aged care homes. But I really loved it. And I realized that. Well, it took me a while to realize, but I realized that's kind of the space that I want to be in. I found that the marketing comms people in that space, they really already knew why video was so important. So I wasn't having to try and sell people on, like, why you should buy a video, because, like, if you're not using video in 2022, like, I'm not sure I could convince you to. Yeah, so that was one. And then I just found the work really fulfilling as well.
So that was another part of it. But it definitely presented a new opportunity. And I started to realize that manufacturing and transport, I still can work in that space, but maybe that's not where my marketing needs to go. And then I thought about the types of people that I was really working with, and they're pretty much all marketing and communications people. And so I started to think a bit more deeply about. Right. How do I market and work and guide more marketing and comms professionals in video? Because that's what I love. Doing their job. Video is only one component. So if they've got someone who can just tell them what they need to do to get what they want, that makes their life so much easier. And I've had some real success almost since just switching immediately. Something just happened in the way we're working and the way we're communicating just seems to be working a lot more smoothly, if that makes sense.
Yeah, you know, we talk a lot about in the VBA about you want to get to a no as fast as possible. And when it comes to sales and marketing and the mindset around that, sometimes you have to go down a road that you believe is the right road, but actually what you're figuring out is that it's not the right road. And I don't think any of that's ever wasted because you still have a decent number of clients in manufacturing and distribution. But I think what's great is that. And we've often had this resistance. People talk about their fear of a niche. They fear going too narrow because they think that other opportunities won't come in. But even though Lyft was very squarely focused on manufacturing, distribution, those kind of industries, someone saw your work on LinkedIn and said, hey, do you guys ever do any of this kind of work? And so tell me about that, because I think there's a lot of resistance in the physical videography space against niching. Everyone wants to be kind of like all things to all people, but it doesn't work as well as niching because of the focus. And your focus on one industry opened up a door in a completely different industry, which is now a route that you're sort of forming.
Yeah, yeah. For us, I think I've always kind of believed that a niche would work. Like, when I look at other successful agencies and companies, generally, they've got a niche that they're working in. And that's kind of where I was like, right, we'll try the industry approach. And it just didn't work for us. I'm sure it has worked for others. And so I'm finding a lot more success with the sort of focusing more on the person as well, particularly in the healthcare kind of space. So. But changing niche.
Yeah, I guess. And using LinkedIn to do that, is that kind of what?
Yeah, I mean, because I'm just. I'm just curious of, you know, how you've done it, because you've really. You've used LinkedIn very squarely, but your approach has been niched on an industry and it wasn't quite working out the way you hoped it had. But out of that blossomed another industry and it didn't really take a lot to just go, well, we'll go down this route instead.
No, it was pretty easy to pivot. And I remember we had a call, Dan, and I was like, oh, my goodness, I've spent a year doing this thing and it's not working. What? Oh, my God. And then, you know, a couple of weeks of like, just changing how I was posting on LinkedIn, connecting with comms and marketing people in health, community services kind of space. And suddenly it was like, kind of like, oh, it's actually not so bad. People don't really care. No one really remembers that I was the engineering video guy. Everyone's moved on. I've moved on.
And I think that's. That's the key, is that I think it's creatives. We can get very hung up on our identity and feel that, but we are known as this person. And you hit something very, very key there, Graham, which is nobody actually cares about you. Like, they don't care about themselves and they care about the problem they've got to solve. And if you're posting about manufacturing or distribution and they're in health care, they're probably not even registering it. But as soon as you say health care, Marcos helping you do X, Y and Z, they're like, oh, that's the guy I need. And I think that's a really valuable lesson because I remember that having that meeting with you and you were. You were pretty down on yourself. You were pretty kind of like. And I think this is what's important to share, is that business is still a roller coaster, but it's a. It's a mindset roller coaster. And. And sometimes you do hit rock bottom and you feel like, oh, God, if I just wasted all this time. But I think you'd agree you never really waste time getting to a.
No, because I wish I got there faster, though.
Exactly, exactly. Don't we all? But that's business, right? And, you know, it's not an easy ride. And if it was, more people would do it, but it's not easy. But now you're in the healthcare space as a key focus. What have you been doing to sort of shift your focus, your marketing focus towards that? Because you were pretty heavily invested in manufacturing, distribution, and now you've just kind of changed direction ever so slightly. What have you been doing to modify your outreach and modify your marketing?
Yeah, do you know what? It actually didn't take much to modify it. Basically, a big part of our, I guess, outreach and marketing is through LinkedIn. So it was just a matter of changing our headlines, our profile, profile page, all that kind of thing, to our new sort of headline and I guess new branding, even new branding, just tweaking the copy, really, to target a new sort of nation area. And then in terms of connecting with people, I just started connecting with marketing comms managers in health and community services, started to build up a bit of an audience there, continually, continuously post content. So I Aim to post two to three times a week. Um, and at the same time while I'm doing that I'm cold messaging those new connections as well. Um, and I think the biggest thing about if you can manage to post and message people at the same time you become kind of almost like a warm lead in a way because they've started to see your posts and they're like ah, now this guy I've seen is messaging me. And so I found a little, a bit more I guess of a reception when I try that.
Well I think LinkedIn's also, it's a business to business platform so people are expecting to do some business together. And what kind of things are you saying to them? How are you? Because I know a lot of people worry about what they're going to say to someone because they're trying to balance connecting without being too salesy and at what point do they start talking about business and work And I think a lot of people would find that quite daunting.
Yeah, I mean so basically I just, I don't immediately slap them in the face with a pitch or anything. It just kind of starts off with a connection and I just say hey, you come up as a linked on my LinkedIn profile as a suggested connection we work with comms and marketing managers in insert your space to create video content and would love to find out a bit more about what you do. Would it be okay to connect on here? Cheers. So just, just that's my first kind of message which I think I got from your training den and you know that's, that's all you need. I think that's, that's fine. And then generally it's still what like out of maybe like 20 out of a hundred will connect with you. So it's still a numbers game. And then I leave that for a few days, post a bit of content, hopefully they've seen some of my content and I send sort of a follow up if they haven't replied. So yeah, it's just a matter of checking in and consistently connecting and messaging your LinkedIn connections.
Yeah, and it definitely is a numbers game and I think that's something that you know, I wish, I wish there was, I wish to teach that at film school because.
It'S, I think one of the challenges with being a creative is we're not very good with rejection, you know because we come to every project as someone who wants to help, wants to provide a great service. And of course sales involves 80% rejection if not more. Most people aren't interested in what you've got to sell. But I think once you can get beyond that, when you start to ramp up a hundred connections a week, that's 20 people a week that are now on your radar, at the very top of your funnel, and are becoming more familiar with you. And you're absolutely right that the combination of content and connection is gold. And I think you've really.
You know, really gone to town with that and made it a habit. How hard was it as a creative to build some of those habits around handling the mindset of this isn't working and then continuing to reach out to a new market? Was. Was that hard at all?
Really hard?
No.
Yeah. It just took a. A long time to build up the habit of consistently posting, consistently reaching out. And of course, when I was Grant Jamison Videography, or when I was kind of still transitioning, even, you know, I'd be on a shoot for three days of a week and I'd be editing the other two. And I just. I wouldn't do it that way. So now that I've got our videographer, he handles most of that work. I've got more time to focus on building those habits around reaching out. Because if you don't do it for a few weeks, well, then it's kind of like a lag. And then you find, you know, in a couple months time, you haven't done any marketing and you've got no leads coming through. But it's also a time game. Like, I just had one LinkedIn connection I connected with 18 months ago, and we'd been talking, you know, kind of on and off, and now finally we're talking about a pretty big project, you know, so it's just a time thing as well, I think.
Also, I remember early on you commenting in the VBA about.
I think we actually. We actually kind of laughed with you on the fact you were like, oh, I don't think this LinkedIn thing's working very well. And I think you've been doing it for about a week and a half. Reached out to maybe 12, maybe 130 people, 140 people. And you were like, I'm not sure it's really working. I only got three leads.
Yeah, that's crazy. I don't know what happened in that first. The first, like, two weeks, I managed to get like three calls and, like, I think two jobs out of it, but I haven't managed to hit that. I think that might have been a bit of a fluke because those ones were like, hey, actually, Grant, we do need a video, can you give me a call? And I was like, oh, this is easy. What's everyone worried about? It wasn't that easy.
Well, look, mate, we're running out of time for this episode, but I'd love to get you back to talk a bit more about your LinkedIn strategy, because I've watched you really kind of invest in it, not just in terms of financial, but actually in time as well. And I think your LinkedIn game is now absolutely on point. So maybe we'll get you back next week to share a bit more about that.
Sounds good. Thanks, Dan.
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