8 Dec 2025 · 33 min
Den Lennie, Khaled, Andy, and Matt talk about moving from freelancer to business owner. They focus on how your identity has to shift, why community support matters, and what it costs to invest in yourself and your work.
Chapters
Identity. The identity we all have when we transition from being a freelancer to starting a business. That sort of strange period where you're kind of neither either one or the other, but also how that identity keeps shifting as your career progresses. You know, I was a television cameraman for lots of years. That was my identity. Then I moved into rental and sales and when I bust my legs, I was no longer, I didn't. No longer had the identity. And then, you know, moved into doing some coaching and that became my identity. And, you know, that identity keeps reimagining itself. We keep re envisioning the way my identity flows. But. But I'd love to hear from you guys like your identity and people you hear from or talk to in the line of work that you do. A lot of people look up to you as leaders. They kind of come and they DM you and they ask you questions about your business. I know Andy. A lot of people see what you're doing in the building space and they're like, ah, just you. Or I love what Andy's doing and it's so amazing. But this, this notion of identity. Who wants to kick off what that, that word means to you?
Yeah, I'll jump in. I got a good origin story of the, this kind of. The start of this transformation for me was when my bookkeeper came to Bendigo. She was based in Sydney and, and she just was traveling around seeing all her clients and, and we weren't doing well like we were. I had a business partner at the time and we, we were taking home.
And she sat us down and she was like, look, guys, you are going to have to be. You can't just run this thing like a couple of kids having fun making videos. You're going to have to know the business of this, the science of this business. Like, you're going to have to be business people, directors of a business. And, and I remember having a bit of an internal turmoil about that because I, I heard that and I was like, oh, but I'm a filmmaker. And I was, I was resistant to it because I was, it made me feel uncomfortable.
Right.
And I, I ended up going away and thinking about it and really.
Transforming the way I looked at who I was professionally instead of looking at myself as like, my value comes from the fact that I'm a creative and I'm a, I'm a filmmaker.
Businesses. In opposition to that, I had to think, man, what are my goals here? Like, what am I, what am I actually shooting for? What am I building? What am I growing and that started a journey for me of understanding and leaning into the, the art and science of business and getting really excited about that. And so now, like, I'm. That's the part of work that I love the most is selling. It's communicating. And over that, you know, period of maybe five, six years, I've distilled it down to like, who I am is. I'm a communicator. And so what I bring to business, I'm really great at sales. And I love communicating and connecting the dots. And so, you know, that's, that's a bit of my transformational journey of, from seeing myself as a, as a. Just a lowly or, you know, not lowly, but really as a creative. And I don't do numbers, I don't do business. I'm a filmmaker. To know, in order to get where I want to go in life, I have to understand these things, even though they weren't my natural kind of bent. I need to understand them and I need to value them. And so now, now I'm a business person, I'm an entrepreneur, I'm a great communicator. But yeah, there was that separation right from, from my value is not connected to how creative I am.
Do you think we.
Are worried that if we stop identifying as a filmmaker, we lose that connection to our herd, which is like, we're all kind of starving artists together.
Yeah.
Yep, definitely. I think the connection between identity, your sense of self and your sense of value, your self value is a massive one. And if you, if you feel like you're, you're, you know, you identify with a group of people, filmmakers, natives, then, you know, it, it makes sense of where you, where you're at. Like you say, you know, there's that, that idea of, you know, a starving artist and that, that makes people feel better about being a starving artist. I think.
What do you guys think about that?
I, I 100 agree. I think it's that, you know, we all start out as practitioners, right? We like holding cameras, shooting stuff, editing. And then there comes a point where you are looking to either grow a business or start freelancing. And you get busier and then you've got to start hiring other people. And it's that real tipping point of like, at what level do I identify with this process? And for me, like, I've been running my company for almost 13 years now. And it is, you know, I look back on it really fondly, but it was a very gradual point up until I was like, now I'm going To hire help and have them part time, full time.
And then this is a business.
I'm no longer Matt the video guy. And it's like, no, Matt the business owner. And I think that, like, you know, I might be projecting here, but I think there's an element of, of people feeling like it's a sellout where you all of a sudden become a company and you're like doing corporate work and it's not like narrative film doing the film festival circuit and stuff. And it's like, there's absolutely no issue with becoming a business owner. In fact, I think it shows a real strength of character that you're able to help and support and serve a client base with video, with communication. And so I've really found that the part I identify with the most is as a leader and as a mentor and as a pointy end of a business that could help facilitate not only clients needs, wants, but also a team and see their skill set and their careers grow and flourish as well. Because I was a good shooter, I was a good editor, but I was never the best. And I worked with people that clearly just, they loved cameras and they loved lenses and they like spoken f stops. And I was like, I don't care like it as long as it looks nice and tells the story. Then let's move on. It's like you then can create an environment where the work you produce as a team and as a, as a company can be really great. But it's elevated because you can surround yourself with all these amazing practitioners that didn't want to shoot or want to edit or want to whatever. And I can now be that sort of overview, arbiter of taste kind of vibe that like, I can really get invested in the people I work with and see their skill sets grow and develop. And that becomes hugely rewarding for me. It's the collaboration and it's the, the involvement of other people that I absolutely love. And you don't get that by becoming just the videographer and keep staying really small. You have to lean into that as an identity because if that's not authentic and you don't have people's best interests or career goals in mind and you're not actively, you know, supporting that, then those people will leave and they'll move on and your business will flounder and not grow because of that. So that is an identity became so crucial for me to just live and.
Breathe day to day.
And I think when you've all met my team, I think it's really clear that there's no bullshit in it. I care so much about them as though they are literally family members and they know that. And so we all come to the party knowing that I have their best interests at heart and we just happen to make videos as well. And that's awesome fun. So it's one of those things that, yeah, embracing that identity really just gives you so much more freedom, but also security in knowing what you're doing and how you're going about it.
Yeah.
What about you, Andy?
I think. Yeah, I love that. Wow. That was so touching what you just said to him. That.
But for me, like, when I think of this, and I think for a lot of the viewers near and probably where they're at in terms of like transformation.
Where a lot of. Where I believe like a lot of the transformation needs to happen is more in the way that they conduct themselves. So like this, this path that we walk on in business requires us to take risk. It requires us to take imperfect action.
It's. That is actually a requirement. Like, that's a non negotiable if you want to win in business.
You know, you, you've got to adopt that, that, that mindset where I will be willing to be. I'm willing to be wrong. And it's not about being right. It's about things working. You've got to have a mindset where you're willing to get coached and you got to get a. You got to have a mindset where it's. I'm open to somebody else coming into my life and into my business, picking it apart, pointing out all the things that you're doing wrong.
Cop a couple punches to the chin and then smile and say thank you.
Yes.
That's literally what it takes.
Yeah, it does.
We've all taken our fair share of punches to the chin.
You're up.
Solid mouth is Joyce.
But it's true, like a lot of. And this is the common trait in creatives. And I might be pissing off a lot of people here, but a lot of creatives have got like inflated egos. They've got big heads and they think they're amazing. And it's like, you're probably talented at what you, what you do, but that doesn't mean you still can't learn and there's no room for you to become an even better creative. And they almost get in their own way by not being open to learning and adopting other methods. Because success leaves clues. But it takes somebody to find the clues, pick them up, read the manual and be like, I'm going to do that. Not many people can do that. So for me, like, yeah, transformation is, is more in those things because it's like even now, like I'm having to constantly challenge myself. But even if you think of the mechanics of challenging yourself, some people can't even do that. Sticking to a gym routine, sticking to like an eating plan, just things like that. Yes, that's outside of business. But those traits outside of business are highly reflected within business.
So. So in there, there's quite a bit of, there's quite a bit of work that needs to happen. And it's not trying to make the road sound scary, but here's the thing, right? This is the power of a group. And I think then we were talking about this the other day. The thing about growing in business, it's like there's so much strategy and knowledge and wisdom out there, right? It's not a lack of strategy or knowledge or tutorials that we have. It's a lack of accountability and uncomfortable action that stops people from moving forward. So the power of, power of being in a group is, and that's more specifically like a group that's moving towards the common goal. For example, the vba. Everybody within the VBA has invested dollars. They are there for a purpose, to grow their business. A part of growing your business is growing yourself as a business owner. And when you're in a room filled with people who are all moving towards that common goal, you will more likely hold yourself accountable to the better version of yourself. And it's the better version of yourself that you need to get to where you want to go.
So that's so good, Andy.
It is, it is.
Because like the.
It'S like, oh, you made me think of it, right? Like it's the how do you transform? You're talking about like people. We're not islands, you know, we are made for community. And you can only bring yourself to where you're going. And so there's a, there's a point in, in your own decision making framework that where you go, I need some outside investment here. I need some help. I need to do this with someone else and draw on experience and put someone in my life that is going to be able to speak things that I maybe don't want to hear sometimes and provide that accountability, like we say in the army, that you, you two, two or more people can produce and accomplish more than the sum of their parts. So it, you know, two, two people working individually will be able to achieve so much, but if they work together, they will be able to achieve way more. And that like, I think you've laid it out beautifully there in, in the power of community that is going in the same direction, you're able to transform yourself so much more effectively.
Yeah, I also think before but you're.
Go and like the inflated ego of the creative. Right. And I think there's a, you know, there's so much pride that's misplaced in the like I know everything and I have the answers, but the ability to show up and go, you know what? I don't know, please somebody help me I think is hugely, hugely valuable in this, in this transformation because I think there's like, there's a time and a place for kind of the fake it till you make it. You sort of leap into the, you know, jump into the deep end sort of stuff. But when it comes to business and essentially keeping somebody's livelihood, whether it's your own or greater teams, like there needs to be an accountability to, you know, accuracy and doing the right thing. And so fronting up and saying, hey.
I'm going to put my hand there.
I have no idea how this works or how to do this. Somebody helped me point me in the right direction. What are some resources available to me to help is like the first and greatest step. And it can feel so terrifying because it's you then putting yourself out there. It's a vulnerable position but you find the right community, you find the right mentor, we find the right collaborator and then all of a sudden it becomes that, that cushion of hey, I've got you, let me support you through this and help guide your hand. I had a, a friend of mine who went to an information night for a fringe festival, like a sort of, you know, cultural art, little things and it was like a. How do you go about registering for this event, getting venues, blah, blah, blah. And in this room somebody put their hand, they're talking about like the marketing for your show and how to kind of make, you know, it enticing to pick another talking about, give me a marketing copy. Like this hand goes up from this, you know, bright eyed, bushy tailed young person and they're like, hi, what's copy? And it's like to us who sort of deal with marketing and like marketing copy all the time, like we know that it's expected and understood. This person had no idea. But also ask the question and they're going to be better for that. And I think it's such a beautiful thing to be able to say, I don't know, please help Me, it just is such a great mindset shift to move you and, and your work forward as well.
That points to your own value. Right? If you, if you are, if you think my value is in that I know lots of things, then you know, there's a, there's a self consciousness that will prevent you from learning, it'll prevent you from sticking your neck out and going. Might be a silly question, but, you know, what's this? If you can separate your identity and your value from the fact that you're, you think you should know everything and you want to come across like you're the, you know, the expert in all things, then that's a massive required element to starting a transformation journey is just owning the fact that you know you don't know everything. And what that, what that does is it enables you to bring curiosity to every situation. Like that's, that's how I manage.
Lots of client. We work in a lot of different industries and that's how I build rapport. It's how I, it's how I communicate really well with, with clients. I make them feel understood by bringing curiosity and not just sitting there and smiling and nodding going, yeah, I know what you're talking about, but I actually don't. You just ask a question. Right.
I think also it. Having been in a lot of different communities myself, you know, there's a lot of, there's a lot of videography and filmmaking communities on Facebook, for example. But one of the things I observe is, and a guy just joined us last week said, oh, you know what, I've been in a bunch of different Facebook groups, but you always get the feeling people are holding something back and you can't really unlet go and ask deep questions because he said, really secretly, you're worried that something else is going to steal your clients. And so I think that when we created the free community that we invite people who listen to this and watch us to join, there'll be a link on the page.
It's a place where there's no charge to be there, but you do have to commit to being there. And I think that's the difference. It's not just like when we used to have a community on Facebook, I'd look at people wanting to join and if they were a member of 50 other groups, I wouldn't let them in. If they're a member of half a dozen groups and this was the only video one, I'd let them in. So I think there's a great expression that a friend of mine, Ben Simkin. The first person I heard it from was Ben Simkin. He runs Business Net. He's a Facebook marketer. He said the majority is almost always wrong.
I've always grown up kind of on the outside of the cool kids. I was picked on at school. I've always been sort of isolated. So all I've ever known is being on the outside of the circle. And I think that's the reason I'm an entrepreneur, because I'm very comfortable being out of the comfort zone of a group of people who all say the same things. And the specific example I'm thinking of is so much recently I've heard from freelancers. Oh, yeah, I've been speaking to a lot of people and it's really quiet out there. And I'm sitting there thinking it doesn't make any sense because everyone that I work with in the VBA is busy, as they're all busy. They're all working, they're fighting off work. I think there's two things. One is because they've made the commitment to changing their identity, to accepting that business ownership takes doing stuff you don't necessarily want to do. But they're all busy. And I think one of the reasons that people feel safe in a Facebook community of videographers is, hey, we're all the same. And we can all agree that it's quiet out there because there's safety in numbers. Like I heard being attacked by a lion in the savannah, hard together to keep each other safe. But if one little one gets out on the side, no one's going to save it. They're like, all right, sacrificial lamb. And so I think that the quality of your network is equal to your net worth. And that's a very well known saying. But I think choosing the right environment to spend time in. And the truth is, those that do decide they want to go deeper and end up in one of our paid programs have a deeper experience because they've committed financially and also more than any financial commitment, they've committed emotionally to the growth journey. But I just wonder if any of you guys have noticed that, like, with some of the free groups that maybe exist on Facebook, where there's a very low barrier of entry. Have you noticed the kind of levels of conversation that happen? And it's almost like we want to be seen. Like we're all mates, we're all helping each other, but secretly.
They'Re terrified.
Yeah, there's a lot of justification of issues and, you know.
Relating and connecting over, you know, problems.
Or reasons why things are hard. I. I'm. Thank goodness. I'm not really. I don't spend much time on Facebook anymore. But one of the things I love about the communities that I am involved in and the VBA being the biggest one, is that there's a shared understanding that we are growing towards something. And this is a big key part, right? Nobody in there has a limited. A lack mentality or a limited view of opportunity. We're not sitting there going, well, there's a only, you know, there's only so much work out there.
And.
And if Matt gets some, then that means. I don't get that some. We. It is. That community is built on the understanding that there is more than enough work for everybody. And why is that possible? Because everybody's different. I. I'm never going to be Matt, and that's great because I like me, but it's. There's an understanding and a shared kind of value that we're happy to collaborate, we're happy to share because there is more than enough. And if I help someone else grow, then I get some good vibes from that. But then I know that that community is going to be feeding back into me as well.
Probably you, Matt, have you. Have you experienced any communities? What do you notice when you. When you speak to other freelancers? You know, maybe you must hire a lot of different freelancers. You must come into contact with a fair few people. What do you observe?
Yeah, I, I think it's a. Authenticity is a big one for me. And I think that, you know, if there's a. There's a barrier to entry, whether it's financial or experience or whatever, it's the sort of vetting process of bringing somebody into a community to show that, hey, I'm authentically interested in this or want to contribute in a meaningful way, just means that the quality of that contribution is so much higher. I think that, you know, the. Yeah, everybody knows Wikipedia has information on it, but the quality of that information can be contributed to by anybody at any time. And it's sort of just a bit of a wild west, right? Whereas if you go to an encyclopedia or a source of information that's. That's tried and tested and really focused on that one thing, you know, you. To get some reliable information or pointers. And I sort of look at that like a. Like a group.
Right?
So it's no secret we're all part of the vba and we will come to that with an idea of how we are expected to conduct ourselves. But also there's an expectation that we'll show up and ask questions and be vulnerable and want to know how to get support for certain things we're dealing with. If I went to a generic business advice group, I'm not going to be experiencing the same things as other people. And the advice that's getting thrown around might be coming from a completely different perspective or a completely different approach or mindset, you know, to kind of come back to that mindset and identity. It's like, you know, we all share a common theme of being video production business owners and we all want to see it grow in a way that's. That's repeatable, that's scalable, that's sustainable with team and make sure that their contributions and careers grow and succeed along with that. That there's such an alignment to the advice and to the conversations that we'll have, that it's such so much richer for it and so that community so focused on that that it's going to be the best source of information for that. I could ask the same questions of another group and get completely different answers because there's not that same alignment and understanding. Finding, finding your herd, finding your tribe, and really just being invested in that community. It's so incredibly rewarding.
You know what you will get from a lot of free groups, and it's a bugbear of mine, is you'll get the haters. You get people in there that just want to, you know, you throw something out there and they just pull you down or like, they'll be like, they're just waiting. They're just waiting there. Keyboard warriors going, ah, gonna attack. It's even like, it's no fun.
I've been selling a bunch of stuff at home and some of it we've gone, let's put it on Facebook Marketplace. And it's like Mad Max wasteland out there. Like, everybody's coming in trying to lowball you, like fight you on price, like a whatever. But then you go to ebay and it's like, it's a curated environment. Everybody's come to have civil conversation. It's a different selling stuff in both places, but it's a far different experience because of the community around it. Who would have thought I'd bring up.
But ebay charges for its service and people who are cheap don't want to pay. So they'd rather fight on marketplace and deal with all sorts.
Than just pay a few bucks to do it in a way that's respectful and more value. There's more security on face and on, on ebay, you know. How about you, Andy? I mean, what's your experience of, you know, being in communities? You've been in a few different ones. Does this, does this resonate?
Yeah, like if I try to keep this on topic in terms of like identity transformation.
I think like Matt kind of summed it up and Khaled is touching on it. But like in a nutshell, like if you just zoom out.
You.
Want to.
Surround yourself with others.
Who are holding themselves accountable to a better versions of a better version of themselves.
Right.
And where are these people? They're not in free groups. These people are in.
Paid coaching programs who are focused, zoned in on making progress. So I mean it's not like, yeah, it's a bit of a no, it's a, it's a, it's like a no brainer. And I guess the question everybody should ask themselves is what, what pace do I want to pursue this journey? Because you can hop from free group to free group to $47 a month group, you know. But I'll tell you what, man, my biggest transformations came the first coaching program that I invested in ever. I paid 15 grand. And, and mind you, this is early days expansion media where I had like, that's a lot of money for me, but I'm like, I made the conscious decision that I want to play this game. I'm serious. So where are all the serious people at?
You know, that's, that's just, just how you got to look at it, right? And when you make that click of where all the serious people at, you're not even looking at free groups. Why the waste your time on a free group? You know, like let, let's, let's go make some, let's, let's get serious. You know, the free group serves its purpose. It's, it's a part of, you know, raising awareness, identifying a bit of value. Okay, there's, everybody's got their doubts initially, right? But if you're in a free group and you know, you need to take action and you keep procrastinating and then you're like, I'll just try another free group. You're the problem. The group is not the problem. You're the problem.
You'll take your problems to every free group. You'll go, you'll find yourself in. Right.
And, and even, even with a mentor.
Sorry, you go, Dan.
I was gonna say the. And the other thing with the free groups are people looking for free is they're the first to complain about rates because they don't value themselves. And if you don't value yourself, you can't ask a client for money. A number that makes you squirm slightly.
Yeah, that's a great point. It takes a level of self awareness and self value to be able to sit in a conversation with a client and have the money. The money talk.
Yeah.
You were saying this to someone. Yeah, go on. Sorry. We've got going on.
Even with investing into a coaching group or like a paid mentorship or anything like that, even if the coach isn't the right coach for you, you will still learn from that experience. There's still value to be taken from that. I've paid for coaches before that. I was like, oh, wow, this actually isn't for me, but I learned something from it. And I'm like, oh, shit, that didn't open the door for who I need it next, you know, so there's always value in taking that action and, and you know, there's a lot of times in business, there's a lot of uncertainty. Nine times out of 10, we're sitting in uncertainty. Really. Like, there's a lot of time you just got to get cool with the uncertainty and learn how to roll with that. And I think that sort of same muscle works when you're looking to jump into a group where there's others out there and moving towards bigger things. There's no uncertainty, but it's like you'd rather be in a room with people moving towards it at pace.
And after all of this hating on free groups, come and join our free group.
Yeah, let's do some context. It's not on Facebook.
It's not on Facebook. So it's all right. But literally.
You get to find, like you were saying, Andy, like, if you're the free group hopper and you're not ready to commit to anything, then, yeah, know you're going to bring. You're going to find the same problems wherever you go. But, yeah, it's an opportunity to find your tribe.
Right. I mean, and that's not me hating on free groups. We're talking about growth here. Right? Growth. Growth requires certain elements. Right? So there's value in free groups 100%. But if you're serious about making the move and moving forward, come into the free group and then talk about moving to the next level. Because all of us here have done it. We've all invested and moved forward. That's how. That's why we're doing these podcasts. Right? So, yeah, yeah, yeah, yeah, yeah.
We want to see people grow.
I I think the last count I've spent well in excess of a quarter of a million dollars on coaching masterminds education in the last 10, 15 years. I have never, ever regretted a single center. Usually you're doing it at a time when you don't think you can quite afford it, but then when you do push through that discomfort, you realize how much you've still got to work on and then that sort of reality veil drops and you're like, okay, now I know where I'm on the journey and you're out there there on the journey regardless of if you do paid coaching or not. But I promise you, if you are in an environment that is you have to pay to be in, you will. You will take far more action because you've got skin in the game.
When you've got real hard dollars on the line. It's amazing what that does to your motivation to get up and do the work.
So true.
Right, I think that's us for this week, gents.
Come on.
Good to see you all. We'll catch you all next week. Be sure to sort of like and subscribe and all the other gubbins that you do these kind of things, but do come and join our and if you don't like it, you can leave. There's no hard feelings, but there's a lot of great content in there. We're all in there. You can literally ask us anything and yeah, no pressure. Come and come and hang out and have some real conversations.
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