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.