Your Network is Your Networth with Pitchcraft Founder and Award Winning Writer Kelsey Ogletree

In today’s episode of the HN Haus Podcast, our host Hannah Nieves, sits down with Kelsey Ogletree to dive deep into her journey from a top freelance writer to the founder and CEO of the innovative tech startup, Pitchcraft.

Discover how Kelsey navigates the challenging landscape of building a tech company without a tech background, the innovative use of AI in media, and balancing the demands of motherhood and entrepreneurship.

🎧 IN THIS EPISODE WE COVER 🎧 

[00:02:35] - The Birth of Pitchcraft: From Minimal Viable Product to Custom Web App

[00:08:40] - Overcoming Technical Challenges in a Tech Startup

[00:14:15] - The Maternal Edit: Support Networks for Working Moms in Media

[00:19:50] - Balancing Motherhood and Business: Embracing Grace and Harmony

[00:24:30] - AI in Media: Opportunities and Ethical Issues

[00:30:25] - Shift from Freelance Writer to Tech CEO

[00:34:45] - The Importance of Continuous Learning and Networking in Tech

[00:38:22] - Trends in Media: Ecommerce and Diversified Media Outreach

[00:42:00] - Authentic Networking and Helping Others

[00:47:30] - The Future of Pitchcraft: New Features and Journalist Participation

🔗 LINKS 🔗
Follow the Hosts: @hannahmnieves & @maritzatobon
Follow Kelsey here
Follow HN Haus: @hnhaus
Request an invitation to The Thrive Collective
Request an invitation to Maison

Transcript

0:13

Hello, everyone. It's Hannah Nieves of the Agent House podcast, and I'm so excited because I have my dear friend, Kelsey Ogletree of Pitchcraft here. Thank you so much for being here. Thank you for having me, Hannah. I feel like our days have gone by, I mean, like, four and a half years ago since I first met you. And I feel like it the first time I feel like it was Instagram when I commented on your Instagram post. Yeah. Almost, like, 5 years ago. That is just wild. And to see, like, what you've created in the last almost 5 years is just incredible. So for those that are not familiar with you and your story, can you just share a little bit more about you and what you do? Sure. So I grew up in Montana. I was a farmer's daughter and very much a country girl. And then I moved to the big city of Chicago to go to grad school, and I got my master's degree in journalism from Northwestern. And from there, I went on to be an editor at a business publication, luxury lifestyle magazines, and got into travel from the trade side a little bit. And then I got laid off in 2017, and so I committed into becoming a freelance writer. I really, you know, was unsure about that career path for me, but it ended up being amazing. I was able to build a really successful 6 figure business as a writer, and that really grew through the pandemic. And then I decided to launch these kind of like Zoom meetups between publicists and freelance writers. And at the time, no one was really in that space. I had launched a newsletter when I was a writer, really talking about building relationships between those two sides of media. And that was kind of a novel concept back then. We didn't have Substack back at that time. You know, I remember sending out my first email newsletter and so many publicists subscribing and saying, oh my gosh. I wish all writers would have one of these. And now fast forward, you know, 7 years, like most writers do, which is kinda funny. So, yeah, we I mean, I feel like I kinda pioneered a little bit of the freelance writer newsletter and certainly the conversations between PR and writers. And that kind of parlayed into free workshops, and then that moved into paid workshops where I was really bringing in a lot of other freelance writers to talk about how to pitch them and how to work with them. And that was resulting in a lot of success between publicists, like, better able to pitch these writers to really get their client stories told in the press. And that kind of snowballed into this thing where all of our workshops were selling out, and I thought, okay. We really need to create, like, an an ongoing community around this rather than just these one off events. And so in 2021, I developed a membership platform called Pitchcraft, and that has really evolved into a whole, like, custom built software program, web app called Pitchcraft that we, my husband and I now run this together. And our job is really, you know, connecting publicists to writers and editors and producers and all kinds of journalists and content creators out there to really help their clients get their stories told out in the media. And we're really all about building those connections. And our tagline is build relationships, not list. So that's kind of what we're all about now. Wow. It is so beautiful to just hear the story, like, come together like this. And every time I see your name, I always think of the word connections, and it's just so beautiful just from coming from the PR world where it really is so transactional. You know, that industry is very transactional in the way, you know, that they do business and run their businesses, work with clients, and things like that. And it's really beautiful to to see how Petroft is really pioneering this new just even, like, mindset around how other publicists and PR agencies can work together. And I wanna kick off with talking about connections and your network because I talk a lot about that as well. Like, your network is your net worth, and it's really just connecting with the right people, but it's building the right relationships. Right? Authentic relationships. And I feel like you do such a beautiful job at that. So any advice for people that might be listening into this podcast that are just really want to wanting to expand their network? Any tips on just building really good relationships? Well, one thing that is kinda coming up on hearing you ask that question, Hannah, is just what to do when you are in a situation where you're meeting someone new or you're in a networking situation. And I think our natural tendency is to go into those kind of experiences thinking, like, what can I get out of this or what do I need? But you really need to flip your mindset and say, like, how can I help others through this experience? And one approach I take whenever I'm talking with someone new is who do I know that I can connect you with after we talk that could help you in your business? So I love asking people, you know, what what help do you need it right now? Or, like, what connections are you looking to make, and how can I help facilitate facilitate that for you? And that doesn't look like me, you know, doing something for you or, like, me being the person that you need to connect with necessarily. It's me being, like, that liaison between you and, like, someone who will help you to, you know, take that next step in your business or, you know, connect with this journalist for the client. So that's really a great approach, I think, to take. It's, like, not what someone can do for you, but what what can you do for them through a connection that you have. And that really is something that, to me, makes those connections really memorable. And they're gonna remember if that connection that you made for them leads them to something greater. Like, they're gonna come back to you and be so grateful, and that will only, you know, be more fruitful for you in the long run too. Oh, that is so beautiful and so spot on too. What are your thoughts on you know, when you're building and these connections and just relationships with people, do you, like, have any, you know, touch points throughout the year where you're, you know, connecting with those people, like, in your network? Do you do you make an intentional approach to do that, or is it very, like, organic in terms of, like, follow ups or just catching up and, like, things like that? That's a good question. I think it's pretty organic, but there are, you know, certain people that I love to watch them kind of as rising stars and be supportive of their journey from the beginning. And, you know, one thing that always sticks out to me is how can you be a cheerleader for the people who are just starting out. Right? Like, everybody wants to be best friends with the editor in chief of this or the top producer at whatever show. But, you know, can you build those relationships from the beginning and really be authentic in your approach to that and really support that person throughout their journey? And I think we all remember too the people who have done that with us. And I will never forget the publicist who believed in me in my very early days as a freelance writer, invited me on trips, like, would grant me the option to do these amazing experiences that then enabled me to grow and have my violence in these top national publications. So I think it's really just coming from a place of authenticity and always thinking about how you can add value to that person and not being self serving in your outreach to them. I love that you said that too because you can tell, like, within 2 seconds when someone's doing outreach or connecting with you, and it's a very, like, self serving, you know, way versus a, hi. I'm just thinking about you. I just wanna connect. Like, how are you doing? You know? Versus I'm looking to get something from you. You know? So I I love this, and I wanna talk a little bit about pitch craft here because I love the organic flow of, okay, Going from freelance writer to starting pitch craft, you know, was there, like, a tipping point when your identity had to shift from, you know, writer into journalist, a writer into tech startup? Like, what was a tipping point where you're like, okay. I'm actually going to leave this behind and really start and scale this venture. Like, what was that experience like for you? Yes. It was kind of interesting because there were a couple of things that forced my hand a little bit there that I wasn't expecting, and one of them was becoming a mother. And I had my son, my first baby in April 2023. And I remember putting on my out of office for, like, 4 weeks thinking, oh, I'll be back in the game. I'll be traveling. I'll be writing. I'll be pitching. And it didn't happen that way. I just I had lost my kind of drive to be so like, such a top producer in terms of rating, and I just kinda needed some time to recalibrate and really figure out what I wanted to do and where my passions were. And so I kind of took some more time off from writing than I expected. And then when I came back, I was sort of full on in the pitch trap space, because I really was just doing a lot of time reflecting and feeling like my role was more about being a connector and facilitating relationships rather than being one of those journalists that PR was pitching. And so that's been a really big shift for all of my friends in PR who I've known for, you know, the past decade to really kind of reshape my identity to them as that rather than someone that they could pitch. Mhmm. And I was really nervous to do it at first, to be honest with you. And one thing I know you were aware of this, but I had this idea to put on an autoresponder on my freelance writer email that I was transitioning away from writing and, like, full in on pitch craft. And I know it sounds silly, but I was so scared to put that on. And, I mean, I literally had anxiety for, like, several days after opening it. But it's honestly been the best thing for me because it has enabled me like, I had so many people pitching me on a daily basis. It was, like, an easy way for me to market. Like, this is kind of my new identity now. This is what I'm doing. Anyone who reached out, like, knew that I was going into, you know, my full time role as CEO of Pitchcraft and tech founder. And I think a lot of things have shifted over there, and I I'm happy to say that, you know, like, you know, about a year after I did that, I feel like my I am seeing more as a tech founder now, and I do still have that credibility as a writer because that's part of my experience. But just because I shifted into this primary role of tech founder doesn't mean that I lost my credibility that I had built as a writer. And I think that's what I was really scared of, but but it didn't happen that way. And so I would I'm just really thankful for kind of my personal evolution over the past year. Because anytime you're trying to shape your reshape your identity for yourself or for others, I think it's a really challenging transition and one you have to spend a lot of time in reflection about to just really see, like, what reflects the new you. And that's okay to shed those layers and become someone new and leave that past version behind. I love this. And I wasn't expecting to going to go here, but as you were talking about motherhood and, like, identity and shifts, like, how has it been, you know, birthing a human and then also birthing, like, a tech start up, you know, around the same time here, you know, how has entering motherhood, like, helped the growth also of Pitchcraft? Because I feel like even for me giving birth to Esme, I feel like I have become a whole new woman. And, like, the way that I approach business is so different. The way that I approach my time, like, who I am, like, have you had any reflections on, like, the impact of, like, motherhood and your company? Yes. I think as I've stepped into this role of motherhood and realized the need for harmony between working and, you know, your personal life and family, I've really started to integrate more professional development and kind of guidance for our pitch craft community around that too. And so we've brought in a lot of conversations about workflow and, you know, things that you can shed that you're not passionate about, but someone else on your team can do them and really stepping into what you're really good at, you know, working with clients that you really enjoy and whose values you share. And I think that things are kind of really aligning on that front where this is the life that I'm trying to live and build, and that's kind of manifesting in the pitchcraft lifestyle that we market in a way to our members. Because at the end of the day, like, pitchcraft isn't just a tool. It's almost a lifestyle. And I know that sounds maybe a little out there, but there's a certain method to pitching journalists and building relationships that we teach in Pitchcraft that isn't for everyone. You know, you're kind of of this mindset or you're not. And I'm not necessarily here to convince you that our way is better, even though I think it is more fulfilling. It's sort of like a journey of discovery that people have to find on their own. And I think what's been really neat to see is that we have had some members come in who are skeptical of our approach to taking the relationships focus and focusing on people first rather than who and what they write for and about. And they've converted after being in our membership, and I think that's really a testament to the power of shifting your mindset. And so, mhmm, I think that's a roundabout way to answer your question. But, yeah, there's just been so much evolution between, you know, the motherhood journey and and running this as a leader and certainly one that I haven't made you know, have not been perfect in. Like, we all are making some mistakes and learning from them and overcoming a lot of challenges. But I think every day, we're just, like, getting one step closer to kind of this lifestyle that we really want to embody and, you know, build a community around as well. I love that. For anyone in here that is a mother, mother to be, aspiring caretaker, any tips or recommendation when it comes to creating that harmony? Because I really feel like you do such a beautiful job at really just, like, balancing the duality of both. Like, any recommendations there? I think I have 3 that are coming to mind. Just give yourself grace in your work time throughout the day. You know, if you I say to myself now, if I'm at my desk after spending a great morning with my son before taking him to his school and I get to work starting at 10, that's a great day. I used to be someone who was chained to my desk from, like, 8 AM till 7 PM at night, and I've just really let that go. If there's work for tomorrow, that's okay. Like, that's actually a good thing because I mean, you have work to do tomorrow. Right? The second one I would say is, like, take email off your phone because then there's no tempting to respond to emails or be working when you're present with your baby and to just really go all in on, like, savoring those little moments because I'm sure, as you know, they go by way too fast. And, what was the third thing I was gonna share? Oh my gosh. I just I'm all brain, I guess. Sorry. It's okay. We can pause and restart. It's fine. Okay. So I'll just mention to Bryce, you can cut the last part out here. Okay. Sorry. I think of the third one too. Hold on a sec. What was that one I was gonna say? Sorry. Okay. And the third one, which I think is really big, is work with other moms. Mhmm. You know, other moms get it if you have to push a deadline, or if you have to reschedule a call, or you have to make some shift in what you've planned to do. And I have just found that it's so fulfilling to really find the people in your network who are also mothers and try to collaborate with them and help each other out as much as you can. I launched a kind of event series earlier this year that we are planning to continue this fall called the maternal edit. And this is about bringing together moms across the media industry to really, you know, talk about the issues that they're facing, the challenges unique to our industry, and just to get to know one another so that we can all Mhmm. Work together and really find that camaraderie through our industry as well as motherhood. And so that has been really a game changer for me when I am just focusing, you know, as much as possible on connecting with other moms on a human level as well as a professional one. So beautiful. And I think that's so great too to support other mothers that are out there. I'll include the link below for everyone that's listening in that wants to check it out. So going back to Pitchcraft for a second and launching this tech start up, what were, I guess, like, some of the biggest challenges that you've experienced? Because I feel like there's a lot of people in our audience who, you know, are thinking about maybe, like, entering a new evolution of their business, and they're wanting to maybe start a a tech startup or a SaaS product. And I know at least for me building Mason, I've went through so many challenges and experiences. So what were some of the ones that came up for you guys, like, in this process of of building pitch craft? Sure. I think knowing where to start, I mean, it seems really daunting. And my piece of advice there would just be use the technology that's available to you to just start something. Like, create, like, a minimal viable product if you wanna start a company and go from there because you can always build on it, and it doesn't have to be perfect from the beginning. So when we first launched PetTrap, we were located entirely through a site called Kajabi. So it was like a third party platform that we built on. And we customized our site, and, we found that there was a lot of things that we needed that we couldn't necessarily do through Kajabi. So that's when we began considering building with a custom developer. And so a year after we launched, that's when we actually launched our, like, Petrobrasv2, which was our own custom built web app that we are on now and able to, you know, do basically anything we want to because we have a team of developers. But I could have never started there. And I'm grateful for, you know, the evolution of Pitchcraft where we've we've really grown up with our branding, with our platform, with our website. Like, all these little things are just kind of like these upgrades as you learn, and you get feedback from people, and you adapt. And so that's the best part, I think, about running your own platform is that you can really customize it depending on what you're learning from your community and what they need. You know, I mean, the tech thing, I think, is a challenge every single day. Like, I didn't come from that background. I can talk about our content and our strategy, and the marketing, and stuff like that all day. That's the kind of stuff I love. The tech part, the back end, even the terminology is still really difficult for me, and you would probably laugh at the things I Google as I'm in conversations with our development team to, like, understand what they're saying. Mhmm. But it's just I'm just trying to learn as I go, and I know that I'm I'm the first to admit that I don't know everything about this, and I will just stop them sometimes and be like, can you explain what this actually means? Or, like, the implications of doing this because I don't know. Know. And so Mhmm. I even as CEO of this company, like, I am still learning and asking so many questions. And also just connecting with others to learn about, like, how they're doing things or how they overcame challenges. And that really comes with expanding my network in a different way. Because previously, my network has been all journalists and public relations professionals. And with this, I'm really trying to connect with a lot of other founders and women in tech and really be part of new audiences because, you know, they say, like, if you're I I kinda like this analogy saying, like, if you're the smartest person in the room, you need to get out of that room and and go somewhere where you have other things to learn. And, not saying that I was ever the smartest person in any room, but I just want to get in front of different audiences to be able to learn from them in different ways and, you know, bring that back to make our platform as good as it can be. Yes. I feel like, building any type of technology really pushes your patience and your resilience and all the things. I always say that too. You know, it sounds really, glamorous and fun, which it is, but there's also a duality of that when you don't come from a tech background. And just like the education, like the learning curve of going through that is pretty steep. So would love to shift gears here for a second and talk about you know, we talk about a lot about personal branding and PR and visibility and media here. Like, what trends are happening in the media industry? Because I feel like things have been shaking up so much, like, you know, publications are losing print, going all digital. You know, like, things are shifting. So what are those top things that are happening in the media industry? Sure. Yeah. I could talk about this topic all day, Hannah. And I'm actually just fresh off a conference from the travel industry. So have a lot of fresh insight there. I think a couple of the big ones are the explosion of ecommerce. So, of course, we're seeing so many publishers jump on the affiliate bandwagon, which means they are producing roundups of products, things to buy, even trips to book that are part of affiliate programs. Meaning that when a consumer clicks through and buys them, the publication earns a commission. And we are seeing this being adopted by everyone from, you know, USA Today to NBC to even Wall Street Journal in the past few years, and it's really influencing a lot of decisions and a lot of the content we see on-site. So, I think it will be interesting to watch that space and see how much the balance of, you know, revenue for these publications is driven through these consumer, ecommerce stories versus ad revenue and kind of where that is going. I know that strategy is shifting a lot internally for a lot of publications right now. Mhmm. I think another big one is just, of course, with any industry, the advent of AI and how that's going to impact publishing. I know a lot of writers are concerned about how, you know, chat gbt will impact their roles as, you know, not only writers for publications, but writers for content sites. So say, like, an interior designer has a blog. Maybe they used to use writers to write their blog, but now they're turning to AI to analyze all their project notes and write blogs without, you know, the role of a writer. One big development that we've had recently is we're seeing some lawsuits slash partnerships come around the concept of licensing content from these major publishers to be used in chat gpt. So we just saw a big partnership between dotdashmeredith and OpenAI that enables them to essentially, like, give content from dotdashmeritus websites in responses on chat gpt. And a lot of, you know, publishers and, you know, destinations and things like that that are mentioned in those articles are happy about it. The publisher is certainly profiting from this, But journalists on the flip side are kind of getting the short end of the stick here because this means their content is being more widely distributed, but their rates are not increasing. They're not being compensated for that. They're not being asked for permission to share their stories. You know, they're having to sign over all their rates to their content as soon as they submit it. So I feel like that's a really big topic now as well. And then the third one I'll mention is, I think, just the intense need to diversify your media outreach. Like, it's not just about pitching writers and editors. Like, we are seeing, you know, content creators, TikTok influencers, podcasts, so many different types of broadcast, YouTube creators. Like, I think there used to be this great divide in between, like, oh, influencer marketing and then public relations or media relations. And to me, that's all one and the same now. Like, I think we're seeing content creators really step up their strategy. A lot of them are amazing storytellers. And there's a lot of opportunity there to connect with those people through things that are going viral on their channels. And also, like, complement that with more traditional pitching to print editors, to freelance raters, for digital publications, to all of that. But I think that PR is really need to needing to, like, up their skill set in terms of being able to have connections and understand the landscape in all of those areas to continue to drive the goals forward for their clients. That is so good. And it's so interesting that you say that too because I think my mind must have been, like, years ahead when we had our p o PR agency because I always umbrellaed, print media, podcasting, you know, TV creator or influencer marketing actually, like, under one umbrella at the time too, because it's all different traffic sources at this point, you know, for whether it's a service or a product. But I think they're all equally, as powerful depending on how you use them. So I love that. And it's interesting to see how AI is playing a role in the media industry because, I mean, as you know, it's impacting so many different types of industries. So it's interesting to see how people are using it and how these, like, big, big, big media companies are using it as well. So before we close here, I'd love to know, like, what is next for you? Like, where are you taking pitch craft? And, yeah, fill us in. Well, we are really excited for the launch of our new website. We really wanted to, you know, put together an online presence that really reflects our relationships mindset, and I think our new site really accomplishes that. Coming up, we are just integrating a lot more tools within our platform for our members to really streamline their jobs. Our goal is to help people work as little as possible so that they can spend more time doing what they love and being with their family, and also enjoying the work they do. Right? And so if we can save them hours of research time, if we can save them, you know, the the trouble of having to set up all these phone calls with different, creators and journalists that they're trying to reach. If we can bring them intelligence on the latest happenings and, you know, the latest publications that are coming out and where people are going. I mean, we really just are wanting to continue to improve our product to really put them on the cutting edge of everything that's happening in media. And one thing I like to say is that, you know, through being part of our membership, like, we want you to feel that you can have a of the minute conversation with your client, with your colleagues, with journalists, with anyone out there about what is happening in the media industry. And I like to think that, you know, anyone that is from our pitch craft community for, you know, more than just a couple months, like, would have been able to answer your question about what's happening in media the same way that I did or, like, offer even more insight. Because we just really want to equip them with that knowledge and resources to do their jobs, like, easier and better and smarter. So lots of exciting things coming down the line, and we also have, some exciting new things we're gonna be rolling out soon that incorporate more journalists' participation. And we already have an amazing network of writers, editors, producers, podcasters, all of that, that are kind of part of our platform on a passive level, but we have some big changes coming there soon that I don't wanna talk about too much yet, but it's gonna be really, a game changer, I think. Whoo. So exciting. So where can people find you, connect with you? Sure. So join pitchcraft.com is our website, and, you can see inside our platform there and also book a quick demo of our platform. My husband and I do all the walk throughs, so you will get us directly and, really get a personal consultation to see if our platform could be a good fit for, your position. And I'm also on Instagram at join pet craft or at kbogletree is my personal. And I'm also really active on LinkedIn, at Kelsey Ogletree, and I publish a newsletter there just packed with valuable insights from the PR space. And I like to think we share a lot of our best content there for free. So, would love for you to follow along there. Amazing. Well, thank you so much for being here. And if you guys like this episode, please share it. Please tag us so we can connect with you afterwards. And I'll make sure that I drop everything in the show notes for everyone, and I'll see you on the next episode.