How to Sell Without Feeling Ashamed or Insecure. EP #260 - Den Lennie
8 Dec 2025 · 8 min
Den Lennie shares strategies for video business owners to sell confidently without shame or insecurity. He covers maintaining client relationships and overcoming the anxiety that often comes with sales conversations.
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G', day, guys. It's Dan here and I hope you had a really happy Easter. We had four days off here in Australia and it's been just amazing having a break. Today I want to talk about how to sell without feeling ashamed or insecure. This is episode 260 of the how to Scale a Video Business Podcast.
Welcome to the Video Business Accelerator Podcast. Each week, we uncover the secrets to creating a wildly successful and scalable video production business. With your host, Dan Lenny, discover how the accelerator program is transforming the lives of our members at www.videobusinessaccelerator.com. enjoy this episode.
So this is a topic that I think that we can all relate to. I think for creatives, the idea of selling does. Does bring up feelings of anxiety, of feeling sleazy, of feeling like, you know, you're just sounding desperate for work. And this is a topic of conversation that we had in great depth today in one of our coaching calls around the idea of selling as a service. But more than that, it's how do you actually deploy that in practical terms? Because I think that we all have conditioning stories, exact examples of perhaps where we've been sold too badly. And then when we are actually put in the seat of selling our services, there can be all sorts of barriers that come up that create resistance and discomfort. And I'm here to say that, you know, the discomfort is okay. The discomfort is normal because, you know, you're not born a natural salesperson the same way you're not born a natural camera person or, you know, color grading. For example, who here, listening to the show, knew how to color grade out of the womb? I mean, it's not. It's not possible. You know, we learn these skills, and what typically happens is we as creatives tend to migrate towards the fun stuff, the shooting, the lighting, the color grading, the editing, the sound mixing, the sound design, and even the production management to some degree. But the bit that I see most video business owners avoid is the selling. And that's because there's some kind of barrier, there's some kind of block to that process. And so what I wanted to do today was sort of help you understand how you can sell without feeling any shame or being insecure about what you're selling. And the key to this starts with not selling at all. If you go into a conversation with a genuine intent to just say hi and learn about that person. Now, let's split these into two. So the first scenario I'm going to talk about is existing clients. So if you have existing clients, the fastest way to build your business is to maintain a really healthy relationship with your existing clients. And I would say that even some of the best companies I work with at times neglect their existing clients. They don't put enough constant marketing in front of their, their clients to remind them that they're there. The biggest fear I think that we experience as creatives is the fear of rejection. And, and I think it's typical that we will oftentimes be like, well, you know, the client loved what we did last time and they were really happy with it. And we, you know, they know where we are, so if they need us again, they'll call us. But what actually happens is even the greatest relations get distracted. A client might have multiple projects running that only one involves video. They might be on holiday, they might be coming back over a long weekend like we are here. They might be just thinking about a whole heap of other things. They might be buying a house, they might be, you know, thinking about a holiday. And way down their list is the booking, the crew for the video shoot. And so you want to maintain a level of front and center of mind without feeling creepy. And that is something that you just learn with experience. And what you can do is just call people up periodically and touch base and be like, hey, I was just, I was, I was walking the other day and suddenly you popped into my head and I realized we hadn't spoken in a while and I wanted to touch base and see how you guys were doing. How are things now that the world seems to be getting back to some sort of normality? How's business? And just genuinely be interested in that person. The easiest way to be interesting is to be interested in the person you are talking to by asking questions and genuinely seeking to learn more about them. And what I would say here is you must have zero attachment to a sale and zero attachment to winning anything from that conversation. And if you can master that, then I promise you, you will be set for life. Now, where most people fall short is they have stories running in their minds and we all have them, usually from childhood, where it stops us. We overthink the situation or the possible outcomes. And that in turn prevents us from taking the first step. So the first step that you should take is taking the first step of just calling a list of cl. And you know, you could sit and say, I'm going to call three clients this week. If you're really confident, you could sit down and do it in a day. But to be honest, I would just start with three a week. And, and set yourself up, prepare yourself for the call. Take a deep breath, make sure you're composed. Easiest way to stay calm is to take three deep breaths, you know.
And through the nose, out through the mouth, and you will regulate any stress hormone that's coming up for you. The second thing to do is just call up with an open mind and have no attachment to the sale, zero attachment to the sale, and just check in with someone like you would any friend. And one scenario you could play out is, if you were to meet this person on set, what kind of conversation would you have with them? If you were to meet them in a bar, what kind of conversation would you have with them? So take that principle and, and deploy it in a conversation. And if you do that enough times, you will get better at it. Now, you might fumble through the first few calls. So what you might want to do is make some notes of some bullet points of things you want to say. A great anchoring point is, hey, hey, Bill, it's Dan here. I just wanted to touch base and say g' day, or, hey, look, you know, the reason of my call is I realized we hadn't spoken in a while, and I was on a walk the other day and I thought of you, and I had an idea, and I want to touch base with you. Is now a good time? You know, so you can. You can enter the conversation that way and just be human. Further a relationship by being interested in them. Now, to flip this on to cold. It's slightly harder when you don't have a relationship with someone so cold. Sales calls are calls that I regard that would involve you. Let's say you've done some outreach on LinkedIn and someone's interested in jumping on a call with you. That's going to require a little more formula, a little more of a framework to follow.
In order for you to kind of get through that call without fumbling around.
But really, I think for the purposes of today's episode, think about your existing clients, think about people who you've worked with before, who perhaps you haven't spoken to in a while, and reach out to them and write a list and say, well, I'm gonna reach out to three people this week. And that, my friends, is gonna help you build confidence in becoming a better salesperson. Cause selling is a service. But it takes practice. And I've probably done, I don't know, 200 sales calls now. The first few were terrible. It's practice. It's like any. It's like riding a bike. It's like learning to color grade. The first time you try and color grade something, it's a nightmare. You don't know where things are. You're fumbling around. Once you've done it a while, you start using a panel, it becomes second nature. Develop a shorthand. And so if you want to grow your video business.
You must learn to get comfortable with the discomfort of doing sales calls. But you can follow frameworks and you can follow structures. And like we did today in the coaching call for the VBA elite is discuss it with peers. And that's where we are always focusing on the detail of running your business. It's not always straightforward, it's not always easy. And if you want some help, you can obviously reach out to us. We can have a chat and see if there's a good fit there. But meanwhile, guys, go and try that. Go and actually ring some clients, touch base with them and I'll see you next week.
You've been listening to the Video Business Accelerator podcast with your host, Den Lenny. If you are a video business owner who is tired of going it alone and would benefit from mentorship, support and weekly accountability, then mouse over to www.videobusinessaccelerator.com to learn more about how the accelerator program can help you today. Don't forget to subscribe and rate the show over on itunes, and we'd really appreciate you taking a few minutes to leave a review.
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