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There wasn’t a single sector of the economy that escaped impact from the 2020 pandemic, but travel was among the hardest industries hit. Suddenly, it became extremely dangerous to fly on planes, and dozens of countries placed heavy restrictions on who could enter their borders and under what circumstances. Virtually overnight, a $615 billion global tourism industry found itself imperiled.

Kelsey Ogletree had a front row seat to this turmoil. For the three years prior to the pandemic, she had built a healthy freelance career as a travel writer, and she found herself wondering if there’d even be a travel industry to write about for much longer. Speaking to others within her network of journalists and PR professionals, she knew she wasn’t the only one to have this anxiety. 

And so, sensing a need for camaraderie, Kelsey put a call out in her personal newsletter for colleagues to join her on a Zoom call to talk through some of these issues. “I don't even think I said the word ‘Zoom’ because I didn't even know what Zoom was at the time,” she told me. “I just wrote that I'm going to have a video call, and would anyone be interested? If so, just click this link to auto reply and say, ‘add me to the list.’” Within 10 minutes of sending the newsletter, she had over 100 people who expressed interest in joining the call.

Kelsey had to stay up that night figuring out how Zoom actually worked for this type of meeting. “I didn't have a Zoom account. I had so many people sign up that I had to get like a professional account so that I could host all these people.”

That first Zoom session was pretty informal, with Kelsey acting almost as a sort of therapist to ease everyone’s anxiety. After receiving positive feedback, she began hosting more of these calls; at first, they were free to join, but then she began charging for admission, especially once they started to take on more of a structured format and purpose.

By that point, the vast majority of attendees to these calls worked in the PR industry, and Kelsey was inviting on a wide range of travel journalists and editors to field questions about how they preferred to be pitched on stories. She quickly realized there was a market need for a company to serve as a sort of liaison between the PR and journalism industries.

So in 2021 — a little over a year after Kelsey hosted that first Zoom call — she launched Pitchcraft, an online membership platform for PR professionals. By that point she had been joined by her husband Derrick, who left his job in finance to run the operations side of the business.

In an interview with Kelsey and Derrick, we discussed how they built out Pitchcraft’s suite of offerings, their approach to monetization, and where they see opportunities for expansion in the coming years.

Let’s jump into my findings…

Building a network of travel industry professionals

Kelsey didn’t originally plan to become a freelance travel writer; she only made the plunge after getting laid off from her full-time job.

She started out as a business editor for McKinsey & Company and then was later hired at a media outlet called Modern Luxury. “It was really focused on upscale luxury lifestyle —  products, fashion, travel, things like that,” she said. After about a year there, she took a job as an editor at a trade publication focused on meetings and events. It was there that she began to build out her expertise in the travel industry.

Kelsey spent four years at that company, working her way up from managing editor to editor in chief. “People told me that I had a dream job, and it did kind of feel like that was true,” she recalled. “I couldn't really believe that I got to basically be paid to go travel to all these amazing places around the world and get put up at the most beautiful hotels, dine at the fanciest restaurants, and have amazing experiences.” It was during this period when she got to know the PR pros who facilitated these sorts of trips. “Basically, the hotel company or the visitors bureau for a city would pay to cover a journalist’s expenses to come and experience their destination. And then it's basically an exchange of services; they pay for you to come experience it with the expectation that you're going to go back and pitch your editors at these high level magazines and write stories from your trip.”

When Kelsey was laid off from that job in 2017, she was terrified that those PR contacts would lose interest in her as she transitioned to a freelance career. “It was really a two-way street; if you didn't have those relationships, you weren't going to have those invitations showing up in your inbox to go on those trips and experience those places.” It turned out those worries were unfounded; not only did those contacts stick around, but Kelsey also secured a steady pipeline of assignments from top tier travel publications like AARP Magazine, Conde Nast Traveler, Eating Well, Midwest Living, Real Simple, Southern Living, Travel + Leisure, and The Wall Street Journal. Not long after she lost her job, she had fully replaced her salary. 

Around the same time that Kelsey embarked on her freelance career, she also launched a blog she called LTR — short for Long Term Relationship. “It was all about how PR can better understand freelance writers — how freelance writers work, how they make money, and really how PR can improve their chances of working with us.” 

The blog had a corresponding newsletter that, at the time, was distributed through Tinyletter. At first, its only subscribers consisted of people within Kelsey’s personal network, but then she started adding a small section on what freelance pieces she happened to be working on. “I would say, ‘I'm working on this piece for this publication, and I'd love a source who can comment on this,’ or ‘I'd love to find hotels that fit with this story angle I'm looking to cover.’” Almost immediately, signups began to surge as communications teams forwarded the newsletter to their colleagues. “I went from sending it out to a hundred people that first time to growing it to thousands within probably a year because people were just continuing to come and say, ‘oh, I wish more freelance writers would do this and be so transparent about what they're working on.’”

By the time the pandemic came around, Kelsey’s newsletter was a highly regarded resource for most PR teams within the travel industry, and so it shouldn’t be a surprise that so many were interested in jumping on a call to hear her take on where things were heading. But what started out as a few informal Zoom calls soon grew into something much bigger and more ambitious.

Building out a paid product

Within a few weeks, Kelsey added structure and themes to each call, and she quickly realized that her audience would benefit from outside expertise. “That's when I started inviting a different freelance writer every week to come in, and I would sort of interview them on camera and ask them questions for this live audience.” With this expanded remit, the calls were requiring more and more of her time to organize, so finally she decided that she should be compensated for her time. “From March until May, I did it for free,” she recalled. “And then I remember sending an email saying something like, ‘I'm sorry everyone, these calls are going to be ending. They’ve been great, but we're moving on to something different.’”

Kelsey’s first paid product was a series of workshops that she sold for a one-time payment. “I remember I charged $200 and I would only sell 20 tickets, and they would have access to one month of these calls — there was one call a week for an hour.” They were both living in Derrick's dad’s house at the time, and Kelsey was conducting the workshops from a room above the garage. “I had this little table that I was using as a desk. It was very grassroots; nothing about it was fancy or polished in any way.”

Derrick was working at NASDAQ at the time and remembers being impressed that his wife had built this side business within such a short time. During the pandemic, they took advantage of his remote work status and moved from Chicago to Alabama, and he had no desire to move back to the Windy City once his employer announced a return-to-office policy. At some point, they both started discussing the idea of him leaving his job to work with her. “There was obviously demand and appetite for these kinds of calls,” Derrick recalled saying. “So what's a way we could turn this into a long term business that both you and I can work in?”

Derrick left his job in May 2021, and both immediately set about brainstorming the platform that would eventually become Pitchcraft. To run the membership, they settled on the teaching platform Kajabi, which not only provided an efficient way to gate paid content, but also offered several community features. “During the Fall of that year, we decided to go on a retreat to the North Georgia Mountains to kind of put it all together,” said Derrick. “And within those three days, we basically had the entire Pitchcraft community and platform built on Kajabi.”

So what did Pitchcraft actually offer? Kelsey outlined an entire suite of services for me:

• Office Hours calls: These are 20 - 30 minute live calls that Kelsey conducts with a professional journalist or editor. She gave me access to the recordings of two of these calls — one with a journalist named Vaishnavi Nayel Talawadekar and the other from an editor named Crystal Meers — and basically they consist of a brief overview of the guest’s background followed by questions about the story topics they typically cover and how they prefer to work with PR representatives.

• Pop-up discussions: “These are one-hour monthly calls around a specific theme,” Kelsey explained. “For example, we have one about how to pitch in-flight magazines coming up next month, and we're having editors from three of those publications join us in an open video forum.”

• Community: Pitchcraft operates an online forum where members can interact with each other on an ongoing basis. “That was a really big reason that we decided to roll this into an ongoing membership,” said Kelsey. “Back when we were doing workshops, people would say things like, ‘oh, I just want a way to keep in touch with people after this — because not only did they build relationships with the journalists that we were bringing on, they also conversed with each other too, and they just were really longing for that community part.”

• Pitch calendar: “We've basically gathered numerous editorial calendars and media kits from all those well-known publications and centralize those into our Pitchcraft calendar,” said Derrick. “And the unique thing about that is we put a pitch reminder on that calendar 10 weeks before the actual editorial close date, so it’s going to send you an alert 10 weeks before that date saying, ‘hey, you should start pitching that outlet.’” 

• Swag: The Ogletrees will actually mail new members a goodie box of branded items whenever they sign up. “Journalists get sent swag all the time and they're always getting free things in the mail that are cool,” said Kelsey. “So we kind of wanted to flip that script and give PR professionals that opportunity to be kind of surprised and delighted.”

I asked the Ogletrees what incentive the journalists have to participate in these calls. “We pay our journalists for the individual interviews, and then we also pay our pop-up discussion guests,” said Kelsey, “Because that was really important to me as a journalist; people were always asking for my time and my expertise, but it takes years to hone that expertise and you should be compensated for sharing that.” The relationship isn’t purely transactional, however; it’s quite common for a journalist who participates in a video interview to then come back to the community later to find sources for stories they’re working on. “I love building a relationship with these writers and editors so that they continue to see Pitchcraft as an ongoing resource to them.”

So what does Pitchcraft charge for all these services? Between $3,500 and $4,200 a year, depending on whether members sign up for a monthly or annual payment plan. Given this relatively high price point, the company relies heavily on traditional sales techniques to bring in new members; in fact, nobody can sign up for the service without receiving a live demo from either Kelsey or Derrick. “That's because I want to show them the platform, but also I want to make sure it's going to be a mutual fit for each of us long term,” said Derrick. It gives him the opportunity to explain that “they’re going to get out of it what they put in.” 

While any PR practitioner can benefit from Pitchcraft, the Ogletrees have had the most success selling memberships to small boutique firms, individual consultants, and in-house communications teams at resorts and other travel companies. “We feel like Pitchcraft fulfills a need because a lot of those people don't have team members,” said Kelsey. “They’re working remotely outside of their main corporate office.” The community gives them the sense of camaraderie they would otherwise receive from working at a larger firm. 

Expanding into free content and live events

Many online membership companies produce a lot of free content to act as top-of-funnel marketing for their platforms, but thus far Pitchcraft has mainly relied on traditional word-of-mouth and sales to acquire customers. “Heading into 2024, we’re going to be really focused on sharing some of the content that we create in Pitchcraft [on free channels],” said Kelsey, “because honestly we have so much data and so much intel that we are collecting from our writers and editors on a weekly basis, and we think there are opportunities for people to learn from us even if they're not members.” 

They also plan to expand into in-person events. When I spoke to them, it was actually the week after they hosted their first event in Birmingham. “We brought in 20 small business owners that really wanted media training,” said Derrick. “They wanted to get to know journalists, they wanted to know who they should be pitching, what they should be pitching, and what part of their story makes them unique.” The event started with Kelsey giving a presentation on the basics of pitching, and then they brought in seven journalists to participate in networking sessions and roundtable discussions throughout the afternoon. “When we put out the tickets for this event in June, it sold out within two days,” said Kelsey. “We really expected it to be primarily people from the Birmingham area, or at least within driving distance, and we had people flying in from eight states for this event.”

Events will continue to be a big priority for Pitchcraft going forward, and they hope to eventually host a full PR industry conference. For Kelsey in particular, this is especially exciting considering that her last full-time job was at a trade publication focused on the events space. “[Producing our first event] was really a big priority and kind of a full-circle moment for me,” she said. “We just had so much fun planning this agenda for people and it was so well received. We are really looking forward to building this out on a bigger scale next year.”

I really need your help

Did you like that article? I also have a podcast interview with the Ogletrees coming out in a few days. When you add up the time it takes to conduct the interview, perform additional research, write the article, and edit the podcast, it can take upwards of 15 to 20 hours of work for each of these profiles.

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