How a former travel journalist built a paid membership community for the PR industry
Kelsey and Derrick Ogletree designed Pitchcraft to serve as a liaison between PR consultants and journalists.
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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.