1900 – Navigating the World of Publicity with Alice Draper

In this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks with the Founder and Chief Strategist of Hustling Writers, Alice Draper.

Draper Wide

Alice Draper, the founder and chief strategist of Hustling Writers, focuses on making publicity more accessible for under-recognized entrepreneurs. Her background as a self-pitching journalist who transitioned into a publicity strategist provides deep insights into media pitching.

Alice's professional journey began in journalism, where she developed her skills in writing compelling pitches that secured her features in prominent magazines such as Post and Business Insider. Her experiences underscore the importance of visibility and communication in the entrepreneurial landscape.

Alice discussed the concept of rejection. She views rejections as crucial learning opportunities. She has shifted her focus from crafting perfect pitches to increasing the quantity and quality of her submissions. This approach has helped her build resilience and refine her pitching techniques.

Alice also emphasizes the importance of feedback, viewing it as essential for improvement. By understanding the perspectives of journalists and producers, entrepreneurs can significantly enhance their chances of pitch acceptance. She advocates for personalizing pitches to establish a connection with recipients, which she believes is more effective than sending generic, self-centered pitches.

Key Points from the Episode:

  • Making publicity accessible for under-recognized entrepreneurs
  • Background in pitching as a journalist
  • Experience with rejection and shifting pitching approach
  • Importance of building resilience and learning from rejections
  • Asking for feedback and understanding journalists' perspective
  • Personalizing pitches and creating warm connections
  • Company's day-to-day work and Pitcher Power course
  • Importance of building warm relationships with journalists and influencers
  • Working with clients to share transformation stories
  • Emphasizing resilience, empathy, and personalized communication in gaining visibility

About Alice Draper:

Alice Draper has dedicated her career to enhancing visibility for women entrepreneurs who often lack recognition. She established her own business with the aim of mastering publicity to elevate her profile as a premium copywriter. As she adeptly pitched to prominent magazines such as VICE, Refinery29, HuffPost, and Business Insider, Alice discovered and honed her pitching skills, which later led her to shift her focus towards providing publicity services.

Now, with over two years at the helm of Hustling Writers, she has successfully placed her clients in over 500 podcast features, including many within the top 1% and top 0.5% of podcasts.Alice also focuses on the emotional challenges associated with public relations work, particularly handling rejection. Through her weekly newsletter, The Rejection Chronicles, she addresses topics such as coping with rejection sensitivity, fostering resilient outreach practices, and normalizing the emotional impact of rejection. This aspect of her work supports her clients' publicity efforts and strengthens their overall resilience and adaptability in their entrepreneurial journeys.

About Hustling Writers:

Hustling Writers is a public relations firm dedicated to amplifying the voices of underrepresented entrepreneurs by securing them authoritative media placements. Established by Alice Draper in 2020, the firm operates on the principle that effective publicity stems from empathetic storytelling. Hustling Writers aims to shift the business landscape towards more significant equity, focusing on increasing visibility for women and international entrepreneurs facing systemic barriers. Their mission is articulated through powerful narratives that challenge existing disparities in venture capital funding and financial services, particularly highlighting entrepreneurs from marginalized backgrounds.

The firm boasts a talented team, including Tšhegofatšo Ndabane, who, while working towards a Master's in clinical psychology, serves as the Chief Storyteller. Their combined expertise has led to notable successes in placing impactful stories in top publications like Refinery29, VICE, and Business Insider. This approach has not only elevated the profiles of their clients but has also supported them in achieving tangible business outcomes such as enhanced credibility, increased rates, and broader platform growth. Through their work, Hustling Writers play a crucial role in transforming the lives of their clients and their audiences, promoting lasting change in the global entrepreneurial ecosystem.

Tweetable Moments:

01:17 – “We're on a mission to make publicity accessible for under-recognized entrepreneurs.”

04:24 – “Building a rejection resilience muscle translates to all areas of our life, making us more resilient and able to take on bigger tasks.”

Links Mentioned in this Episode:

Want to learn more? Check out Hustling Writers website at

Check out Hustling Writers at LinkedIn at

Check out Alice Draper on LinkedIn at

Check out Alice Draper on Twitter at

Check out Alice Draper on Instagram at

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Josh (00:00:04) - Hey there, thoughtful listener. Would you like consistent and predictable sales activity with no spam and no ads? I'll teach you step by step how to do this, particularly if you're an agency owner, consultant, coach, or B2B service provider. What I teach has worked for me for more than 15 years and has helped me create more than $10 million in revenue. Just head to up my influence. Com and watch my free class on how to create endless high ticket sales appointments. You can even chat with me live and I'll see and reply to your messages. Also, don't forget the thoughtful entrepreneur is always looking for guests. Go to up my influence. Com and click on podcast. We'd love to have you. With us right now, it's Alice Draper. Alice, you are the founder and chief strategist with Hustling Writers. Your website is hustling. Alice, thank you so much for joining us.

*Alice * (00:01:10) - Thank you so much, Josh. I'm excited to be here. Yeah.

Josh (00:01:13) - Please do give us an overview of what you do with hustling writers.

*Alice * (00:01:17) - Yeah. So hustling writers, we're on a mission to make publicity accessible for under-recognized entrepreneurs. I myself have a background in pitching myself as a journalist. So I learned to write pitches to get published in magazines like Post or Business Insider. And early in my career, I found the process of getting rejected very deterring, and it almost made me reconsider whether I am cut out to be a writer, whether I have what it takes to write these stories. And I came across a Facebook group where a bunch of writers were talking about their rejection goal and their goal was to get 100 rejections in a year, and that completely did a 180 in the way I approached pitching myself. for the first time, I was focused on output rather than getting each pitch perfect and hearing. Yes. And that's when I started to see, let's see, real results is when I really started building a portfolio and getting a lot of articles accepted, and then it came with kind of a natural skill of pitching, which is how I ended up pivoting to publicity.

*Alice * (00:02:21) - And here we are.

Josh (00:02:23) - Well, and this is interesting, I think, you know, if we think about rejection, nobody necessarily sets out to be rejected. But yet I think when we look at those who, you know, catch a lucky break or however you want to describe it, oftentimes, you know, whether it's an actor or someone you know, that was auditioning for stage opportunities or certainly in media, something I know a little bit about. you know, it's just, you know, not every part is right for you. Right? And not every, you know, guest expert slot is right for you in the moment either. You're not ready. It's not the right timing. It's just not the right production for you. And that might be hard to hear a no, but can you give us a little bit more insight on that?

*Alice * (00:03:11) - Yeah. So I mean, there are so many reasons why you might be rejected. You could be rejected because they just three weeks ago had someone with similar expertise on the podcast.

*Alice * (00:03:23) - If we're pitching podcasts, for example, if you're approaching a magazine, they only have budget to, you know, get a writer to talk specifically about these three topics, and you happen to not be pitching one of these three topics. So and that's all the stuff we don't really know. As the people pitching ourselves, we don't know all the background context of why someone is rejecting you. And then also the other part of it is we get better by doing like I'm a firm believer that the more we do something, the better we get at that thing. And that thing is pitching in this context. So if you're, you know, getting all caught up in a rejection, you're not giving yourself a chance to get better at pitching and to start hearing some yeses. Because if I look back at my early pitches, they sucked. But the reason why I got better at pitching is because I set a rejection goal. And as I started hearing these nodes and then I heard some yeses, I'd be like, oh, well, what did I do right in that pitch? How can I, you know, learn from that and apply that to more of my other work? And I think building a rejection, resilience muscle translates all areas of our life.

*Alice * (00:04:24) - It means that we are a little bit hot, like, you know, more resilient. And we can make bigger tasks and other areas, not just pitching ourselves, which I think is quite key to success, is putting ourselves out there and making those asks.

Josh (00:04:37) - Yeah. So what do you recommend to say someone that is just trying to get their expertise out there? They're just trying to serve audiences. They want to do so either through the media, or maybe they're working with a digital content provider. And let's say that, well, okay, I'm going to be silly here. Let's say that they use like a press release service or they just blast out, like, you know, a hundred press releases about their new amazing book and they get nothing in response. What went wrong?

*Alice * (00:05:09) - Yeah, I guess a lot of things could have gone wrong. Yeah. probably, you know, if you're and I don't really work in the spray and prairie approach of media outreach, so I can't speak to it as much, I do very personalized PR that's what my team does.

*Alice * (00:05:23) - We spend a lot of time on each pitch and so we get a very high acceptance rate. But like with us, the way I do it is, you know, if we're not getting results, we'll really look back and be like, what? What marks are we missing? If you're sending 100 pitches by an AI machine and you're not getting anything, then I would probably guess that, like the people receiving it can tell it's by written by AI. They can probably tell that it's not targeted and like kind of what they deal with, what their content matter deals with. So I think there's so many things. So you can start looking at about what went wrong. It could be that you're pitching the wrong people. What you're what you released is irrelevant to them. it could be the style of pitching. It could be that the pitching doesn't really address like them in a personable way, because a cold pitch, like, by definition, is cold. And our job is the pitch is to make it as warm as possible so that they're not getting the ick reading.

*Alice * (00:06:20) - It's they're kind of like, wow, this person knows me and they kind of know what I'm all about. And that's impressive. So yeah, I think there's a lot of things that that could, we could spend ages kind of dissecting what went wrong. but I think what could be helpful is ask for feedback. You know, if you do get a no, you could say, hey, like, could you tell me a little bit, what about why? What went wrong here?

Josh (00:06:41) - Yeah. And it's also to having empathy for whoever the creator is. You know, if it's a journalist, if it's a producer is certainly if it's a host, you know, the empathy is they get probably dozens of pitches a day, right. And so don't feel bad because you'll likely got cotton in the wash for them. So it's not that there's anything wrong with you, but to your point, and I think this is really key, we need to underline this. I'm so glad that you picked up on this.

Josh (00:07:15) - You know, I agree with you. Like I found that if you treat journalists and influencers, content producers, podcasters, big YouTubers, if you just treat them like a number and you're going to do the spray and pray approach, that journalist will know that energy. They'll feel it. They can tell like they they know when you're just blasting like a one to many. And so I really like what you said. And I'm a spend more time with fewer people kind of approach. And some people might argue, well Alice, that sounds ineffective. Why am I going to spend all this time with one single journalist? How would you answer that?

*Alice * (00:07:54) - Well, I think, you know, you're not thinking about the long term relationship rewards of that. So, as much as that may take a long time, and especially when you're doing those direct outreaches, it's really hard to kind of make a positive impact in the journalist's mind because they are just getting so many of you every day jumping in the inbox. But when you do have that positive interaction, I mean, the psychology is approvers.

*Alice * (00:08:18) - They're more likely to respond to you over another publicist next time. And the more repetitions you get of that, the more they realize you are a good publicist. Do you know what they're about? You know what they cover. You always come with quality leads. The quicker that pipeline is for you. Getting future clients press coverage from that journalist again. So when you're building those relationships, they can just be like, in the DM, hey, I got someone else I already think she's relevant to, like, what you're working on, and you send it over and you didn't even have to spend time pitching it because you build that relationship. They know you. They trust that you have good people and they like when to see what you're sending them. So yeah, I would think of it in that lens, which is like the long term payoff.

Josh (00:08:59) - Yeah. You know, and I've mentioned this before, but you know, I've had the opportunity to be in the media now over 2500 times. I would say 90% of those 2500 are ten outlets like that make sense? Like I've done so like, you know, so much.

*Alice * (00:09:16) - With the same outlets, right? Oh my.

Josh (00:09:18) - Gosh. Well, you know, it's like I've been a syndicated newspaper columnist since 2009. And so that every single week, you know, it's that's part of showing up. Now, that gig came about from investing in warm relationships, offering to be of service, not selling. And this is what I'd love for you to talk about next, because I have seen a lot of pitches where it's just me, me, me, me me me, me what are you going to do for me? And everybody wants to know because that we launched version 1.2 X of our new software or, you know, here's yet another book, to add to the pile. And, you know, again, those pitches a lot of times sound like, okay, that's great. Well, this sounds like you want to be known for what you do or you want to be celebrated for what you do. There's nothing inherently wrong with that is just that may not necessarily match the goals of the producer or the journalist.

Josh (00:10:15) - Can you talk a little bit more about intent and what makes a good pitch?

*Alice * (00:10:20) - Yeah, I mean, I'm so glad you brought that up because I think that that's one of the quickest ways to get your pitch ignored. And like you said, it's not bad intentions. You know, you obviously when we're pitching ourselves, it's because we think that our work is interesting and relevant for this place. But opening up with a bio of I am so amazing at this thing. Wow wow wow. It really doesn't speak to you. Don't. You're not one. You're not disarming the person receiving it. So they're not like, wow, Josh really knows me. Or you know, whoever's pitching me really got to know me and who what I'm about. So the advice that I always give is a few things to do before you go into the meantime. and this can be specifically pitching podcasts, which is what our expertise is. I would open up with a very specific personal intro, which is like, hey Josh, I loved your LinkedIn post on XYZ.

*Alice * (00:11:16) - I, you know, changed my approach to marketing and now I do this on my social media channels. And now you're like done. Like it's not overkill. They're not being like, I think you're you're amazing. And you have a great podcast, which is very generic and you can probably smell bullshit, but they're like, actually did read your LinkedIn post. And so that that's already disarmed you. Next I would open up with a narrative so it can be a very short. It can be very specific. What I did and what my podcast pitch is. I spoke about my rejection story, which is like me, young, eager journalist. I send a pitch out I like made it perfect. I, you know, proof check, spoke to my sources, did all my research and then crickets. Nothing. And how disheartening that was. And so I think the thing with storytelling, especially vulnerable storytelling, is that you are creating an emotional connection with the person, even if they're a stranger. That's like, okay, this this could be kind of interesting to read.

*Alice * (00:12:15) - Like, this is not my usual just like overkill bio about how you're amazing. We aren't. Even if I said I went to Columbia and spoke to Barack Obama, like, at this point you're probably not even reading it, but a story is just different. So yeah. So I then I opened that, then I would give like the value. Now this is like a speaking point. So if I'm coming on a podcast, if it's an article, I talk about what the article is going to address. And then right at the end I put the bio with the links, make it really easy for them to go check out who you are, where you're hanging out, and then like a call to action that you know you want to connect. So that's my approach to pitching. I kind of go through those steps and I really try not make it feel ego driven and open up with the bio of me. And I'm so amazing because I really don't think it's an effective pitching strategy.

Josh (00:13:07) - Probably not.

Josh (00:13:08) - I agree with you. Your website is hustling Alice. Share just a bit about who you work with and what that looks like.

*Alice * (00:13:16) - Yeah, you know, kind of day to day work as we work on retainer with entrepreneurs, a lot of coaches, a lot of keynote speakers, a lot of authors, people who really have businesses that require them to be getting consistent visibility. That's why I love working with authors, because, you know, they have this book and they need to get this book in the hands of as many people as possible. And then I also have a course called Pitcher Power, which is $57. And that teaches everyone the basics of pitching themselves with the screen shares. And, yeah, like everything that we do in house, how we find the email, how we craft the pitch, all those things. and then I have a free template on my website. so if you just go to, as you said, hustling, you can get that free template with my template, how I do it, all these things I mentioned, you know, about our strategy and like the five key things you should include in a good pitch.

Josh (00:14:08) - yeah. Again, that's hustling And again on that website you'll find those resources. what do I click on to find the template in particular?

*Alice * (00:14:18) - It's hustling forward slash. I think it's pitch template, but I'll send you the link afterwards. You can put in the show notes.

Josh (00:14:25) - That will go yes. So to our friend that's listening. Just click around until you find the show notes. We have a direct link directly to that template, which I think you're going to want because you're probably going to learn some things. Oh, I shouldn't be saying that. I probably should be saying more of this, Alice. You've got it all figured out. And again, your website hustling what would be an example of someone that would make a really great client for you.

*Alice * (00:14:49) - Someone who is interested in being vulnerable to share the story? I think that's like what I love doing is I love kind of getting through to that transformation story. So, if you wrote a book or you're working in the business where you're really about kind of building an authentic brand and kind of showing all sides of you, that's my dream.

*Alice * (00:15:11) - Clients like, I love working with entrepreneurs and recognized entrepreneurs who have done something different in their field. And now I want to show like a holistic, like all sides, the good and the bad, the bad things they overcame in order to get where they are and use that to kind of build up their personal brand.

Josh (00:15:31) - Alice Draper again, your podcast guest placement expert, and you are the founder and chief strategist for Hustling Writers. Your website hustling writers. Com Alice, thank you so much for joining us.

*Alice * (00:15:44) - Thank you so much, Josh. I really enjoyed this.

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