Intro

Welcome to 15 Minute Freelancer, your snack-sized guide to being your own boss and building a business and life you love. I'm your host Louise Shanahan. My LinkedIn bio says I'm a freelance health copywriter. But for the next 15 minutes I'll be tickling your ears with practical strategies behind the scenes stories and nuggets of wisdom so you can create freelance business that works for you. Whether you're just starting out or you've been self-employed for a while, I'll be right here with you to help me navigate the ups and downs of freelancing life. So grab a coffee relax and join me for 15 minutes of freelancing fun. Don't forget to hit subscribe. 

Louise: Hello, freelance fam! Louise here. Today I am joined by another very special guest. I've had a lot of requests to do an episode on cold pitching, but that's not something that I do a whole lot of myself, so I didn't really feel like I could talk with any kind of real expertise about that. So I was keen to get an expert on to share some tips, and I'm very excited to have the cold pitch queen herself, Bree Weber, here. Hi, Bree, thank you so much for joining me. 

Bree: Hey, Louise, thank you so much for having me. 

L: I'm really excited for this conversation. Because as I mentioned before we started recording, I have about a million questions about how to do cold pitching in a way that feels good and actually works. So I hope we'll be able to squeeze them into 15 minutes. But we may need to make this a special extended version. So maybe we could start with hearing a bit about your cold pitching journey. How did you figure it all out? 

B: Yeah, so I definitely started I think the way most of us do, which is just going to the internet and looking for, like, how do I start cold pitching and trying to find templates. And I often got really frustrated that that didn't particularly work for me. But things really kicked up a notch in 2020 when the pandemic hit, because I was one of those people who lost all of their clients. And so I really needed to put my gut into prospecting and try as much as I could to find new clients. And so I treated it as an opportunity to find more aligned clients and projects that I was more excited about. And so I went back to what I knew about cold pitching and I decided, what if I tried this a different way? What if I didn't make this about pitching as many people as possible and waiting for one person to hopefully say yes, but what if I tried to approach it by trying to start one conversation with one person and take it from there. And the result was incredibly effective. I replaced all of my clients within a month, I hit my first 10k financial goal in that same month. And since then, I really just integrated cold pitching into my prospecting process. 

L: That's amazing. It's so inspiring to hear how you managed to turn things around in those early days of the pandemic. It's maybe worth just mentioning here that you're a copywriter, aren't you, just so that people know? 

B: I am, yes. 

L: I think it's really interesting that you talk about just trying to start a conversation with one person. I always had the idea that cold pitching is kind of a numbers game, you know, if you send 100 pitches, at least one or two are going to work out. And I think that maybe helps some people because it takes the pressure off, and you think okay, yes, surely one or two will work out. But do you think that's the right approach? Or do you think it's better to be a bit more discerning about it? 

B: That sort of numbers game is more of a traditional cold pitch approach. But for freelancers, especially when we are providing a service and developing relationships with our clients, I really think about ethical cold pitching, which is the framework that I teach in a lot of my programmes, which is definitely not a numbers game. So those pitches instead of being something templated, that you can copy and paste and send out to you know, 100 folks, for example, you would write that one individual pitch for that one individual person or company that you're really, really keen to work on. Part of that approach means you're very selective and discerning about who you are going to pitch, which means you have a really great opportunity to very intentionally choose your client roster choose who you want to work with. 

So for me, it really encouraged me to go after my wish list clients. So those who are in the copywriting space will recognise some of these names. But by taking this approach, I was able to work with people like Joanna Wiebe from Copyhackers and Peep Laja from CXL. I don't think I would have done that without ethical code pitching or at least not in the same timeframe, because I would have been waiting for them to notice me and come and find me and invite me to do a project with them. 

L: Yeah, I think we're often told that attracting freelance clients is about using inbound marketing and you know, publishing blog posts and all that kind of thing, so that the right clients find you. You're kind of flipping that around and I think the ethical framework’s probably appealing to those who don't want to be seen as too pushy or salesy or maybe feel a bit uncomfortable with self promotion. It sounds like from what you're saying that cold pitching really does work, if anyone was in any doubt.

B: Yeah, so to share a little bit of like some of the stats, I currently have a 100% open rate and a 100% response rate, which is pretty atypical.

L: That's amazing. 

B: And my students who have taken this framework and applied it in their own businesses, and both copywriters and other types of freelancers, see about a 75% response rate. So it's pretty consistently higher than traditional cold pitching, I have about a 60% conversion rate on my cold pitches. And the average that I see with my clients is about 50%, or with students who have taken this framework for themselves. I think not only does it feel good, because you're coming from a really thoughtful, intentional and really compassionate place with each pitch. But I have found that it's actually more effective for freelancers than traditional cold pitching. And ethical cold pitching actually is about building relationships. Each pitch is really just about starting a conversation. And that's really what we're doing when a referral comes our way or inquiry comes our way we start a conversation, and then we move forward towards potentially exploring a project. 

L: Yeah, so it's really about us initiating those conversations with the clients that we would really like to work with. Have you got any suggestions for how we might go about coming up with that wish list of ideal clients? And what kind of approach you should be taking to start that conversation? 

B: Sure. So one of the ways that I got started, because I really struggled with figuring out, like, who do I want to pitch initially, especially if I get to be the selective and discerning and that was particularly challenging. So I didn't really have a defined niche at that time. The first thing that I did was I went into my inbox, to look at the companies that I subscribed to their emails about, the tools that I'm using, the brands that I just really love hearing from, going on my social media to see who do I follow? Who am I impressed by? Who do I admire? Who do I respect? And starting to build a list of names, not necessarily people I know I'm going to pitch. But just people and brands and companies that I feel drawn to, probably because I think what they're doing is great, or there's some sort of value match for me, and then using that to look for themes and patterns and try to find some overlap. And that's what really helped me identify, okay, I really like working with a certain type of course creator, or I'm really interested in the idea of working with really scrappy, disruptive start-ups in the SAS space, right? So you can start to find some themes. And then you can kind of use that as a hypothesis with your pitches to test out is this the type of client that I want to work with? And use that to get some insight as to how you can expand that list, right? And find similar companies, similar brands, and be really selective from that giant list that you have, like, oh, who do I want to work with right now? And what kind of project do I want to work on right now? 

L: Yeah, so you can really dream big, can't you? And then obviously, these people get a lot of pitches, don't they? So how do you make sure you stand out and you don't come across as spammy?

B: The really core idea behind the method that I share is, you're pitching the problem, not your worth. So instead of a pitch that is explaining how great you are, or why other clients have loved you, or touting specific stats, or even dropping, you know, fancy client names, because we don't always have those, especially if we're just getting started. And so instead of trying to kind of prove your worth in an email, which is what I felt traditional cold pitching, was really focused on, ethical cold pitching, is about pitching a problem and then the follow up to that. So basically, kind of step two would be to actually include the solution. And what can be a little bit tricky about this part of the process is, as freelancers, we are not the solution, the solution that we're bringing to the table is the project, the work that we would do. And so part of that process, I think helps to take the onus off of the recipient of the pitch to match your skills match your abilities match your past experience with a specific need, that they already have, or they've already identified. So being able to come to the table with, here's that problem I've identified for you, we can really direct their attention to a problem and then we're starting a conversation around a solution. And so that third tip is when you're wrapping up that pitch include a really small call to action. I often talk about something called a minimum viable ask, which is essentially how can we think of the smallest effort that our recipients can make to provide as an indication that they are interested in participating in the conversation, so for most freelancers that will be asking for a phone call or booking a time in your calendar or even linking them to your portfolio, it'll actually be something that requires less of your recipient, it just still signals their interest in participating in this conversation with you. 

L: That's so smart, so helpful. So what might be an example of a minimum viable ask then?

B: So my favourite call to action – and I'll preface this by saying you have to find what works for you and for your audience – but what works really well for me, because I enjoy it is Loom videos. So after I have crafted a pitch that I feel really strongly about, I'll generally indicate in some way, like I know, getting on a call is really tricky, your calendar is full. So I acknowledge that first and foremost, and then I invite them to tell me about what's resonating in my pitch, if it is. That helps me get a little bit more information about why this pitch might be the right problem for them to solve right now. And then I will generally indicate that I'll share some more information in a little video. And that gives them the opportunity to see my face, see that I'm a real person, see a little bit of my personality. And in that live video that I promised them when they respond, I will generally walk them through a little bit more detail of what the solution looks like. A lot of times, even when I get a positive reply, and the answer isn’t yes, send me a live video, it's no, let's just hop on a call, I think because we're making that minimum viable ask it removes the risk factor of participating in the conversation. We're just making it really easy to reply. 

L: Yeah, I guess they're thinking, well, if I'm gonna watch the loom video, I may as well just chat to you. 

B: Yeah, exactly. 

L: So am I right in thinking that you don't usually include a sample or a portfolio in your call pitches? It's literally the email itself. That is your sample? 

B: Absolutely. So when I first got started, I didn't have samples, I didn't really have a portfolio, I didn't have fancy stats or results. And so that was really kind of the drive behind me trying to figure out well, what's a different way to approach this, right? If you have all of those things, great, traditional cold pitching might be a really good style fit. But if you don't, or if you don't feel like you can rely on them, what else can you do? And so I think part of the approach of pitching a problem and a solution gives us the opportunity as freelancers to showcase how we approach problems and how we solve them, which is really what we're being hired for. And as a copywriter a pitch is obviously a really great way for me to provide an example of me writing persuasive copy, right, but even if you're not a copywriter, other types of freelancers, I think just showing how you think through problems is evidence in and of itself, of how you would show up and work with them. And so they're getting a little bit of a taster in that pitch in and of itself, which is why I think it can be effective without samples and without a portfolio. 

L: Yeah, I think that's a really useful and reassuring way of reframing it for people who are maybe in the early stages of business and don't have the samples to share with people. Or if you're thinking of pivoting into a different industry, and you don't have the most relevant samples. And again, there might be reasons why you have you have the samples, and you don't want to share them. So let's say you've made your wish list, you've sent out your pitches with your problem, and the solution and the minimum viable ask for the potential client. What happens next, you mentioned that you'd had a 100% response rate. So I don't know if you can answer this question. But what happens if you don't get a reply? Do you think it's a good idea for people to follow up? When should they do that? How often? When do you kind of give up? 

B: Yes, I get this question so often, and I am a big believer in following up. And oftentimes the reasons that we don't is because of the mindset piece. We haven't dove into quite that much in this conversation. But it's a really big component of I think why we get stuck, while we don't take action on cold pitching, even when we can recognise that it would be really valuable or at least something worth trying. And then the stage where we have sent a pitch that often feels like a vulnerable act. And we're just hearing crickets. We can create a lot of stories about why someone didn't reply, but the truth is that we don't know why. Maybe they're on vacation, and they forgot their autoresponder, or maybe they're super busy and they just haven't gotten to it yet. Or maybe they've read it 17 times and they are just trying to figure out do I want to jump on a call. So there's so many different reasons that somebody maybe didn't reply, and we don't know what they are. So I'm a huge fan of following up. 

I tend to send my initial follow up within three to ideally seven days, I wouldn't go more than 10 days personally, and sometimes I'm popping it to the top of their inbox. Sometimes I'm referencing back what I've talked about in the pitch and indicating why it's something to explore a little bit further and in the cases where there might be a very natural urgency, I'll follow up to indicate the opportunity to move forward on this, you know, is this something that you're interested in? In terms of how, how many follow ups do you send, at what point do you just say, this isn't working and move on, I think is a little bit variable, depending on your interest in that particular client, like the ideal outcome is we walk away with a new client and a new project. But at the very minimum, we're looking to build a relationship. 

I typically will send two to three follow ups within three to four weeks just to indicate like, I'm interested in building a relationship with this person, that foundation and that relationship is not dependent on doing this particular project together. It's just about having conversation and being willing to connect. 

L: Absolutely. Just because they don't see an opportunity to work with you at this moment doesn't mean they won't come back in future, or refer you on to someone else that they know who may be looking for someone that does what you do. 

B: The most common reply that either I or any of my students have received, whether it's a yes or no, is thank you. Like people can really feel that this is not a typical pitch. 

L: I'm scribbling notes now. And we can put ourselves in their shoes, can’t we, because as small business owners, we're often on the receiving end of pitches, and we know the ones that we like, and we know the ones that maybe don't make us feel so special that have obviously been sent to lots of people. So yes. On that, what are some of the common pitfalls or mistakes that you see people making when they are pitching new clients? 

B: Yes. So I think the number one mistake that I see people making, whether it's traditional cold pitching or ethical, cold pitching, is just that they're going straight for the ask, they're trying to close the sale in one email, and generally doesn't happen in one touchpoint. We can think about it the same way as when you get an inquiry and a referral. And you might have a little back and forth over email, you might have a call maybe a couple of calls. Maybe there's a proposal in the process, right? It tends to happen, or sort of unfold over multiple touchpoints. So we're just flipping the script a little bit. And we are the ones starting the conversation. But we're ultimately going to go through that same sale system that you have set up for anyone who comes in as a lead. 

L: That's so helpful. Thank you so much, Bree. There's just so much in there. I know people are going to want to save this one and go back and listen again. And I can't wait to go and start pitching my own wishlist clients now. 

B: Yay. Oh, I'm excited. I can't wait to hear how it goes for you.

L: So if people want to find out more about your work and ethical cold pitching, where can they go? 

B: So I have a Cold Pitch Masterclass, which walks you through this step by step process of figuring out who to pitch, figuring out what to pitch, doing the research that goes into that process. And then actually writing the pitch and really optimising it with subject lines and a call to action. And all of those points where we get a little bit stuck, along with some of my own examples of pitches where effectively tear them down and walk you through exactly what I'm doing, why it's effective, what's not so effective, and what I would do differently in the future. So all of that is inside Cold Pitch Masterclass, which is normally 97. But for those who are listening, if you want to explore this a little bit deeper, you can grab it at a special rate of $37 if you go to a special link, which is coldpitchcopy.com/louise. 

L: Nice. Okay, we'll put that link in the show notes. So that will be everyone's weekend homework. Thank you. It was so lovely to chat to you. 

B: Thank you so much. I really appreciate you having me on. It's been a lot of fun, and I'm so stoked to hear about how this method works out for you as well. 

L: Thank you. I will keep you posted.

B: Yes. 

L: Okay, that's it for this week. I will be back next week. See you then.

Outro

You've been listening to 15 Minute Freelancer with me, Louise Shanahan, freelance health copywriter and content marketer at thecopyprescription.com. If you enjoyed this, please hit subscribe, leave a review or share it with a freelance friend. And if you've got a freelancing question you want answered on the podcast find me and say hi on Twitter, LinkedIn or Instagram. Thanks, and until next time, happy freelancing!