How An Accidental Discovery Helped One Couple Build A Thriving Niche Community—And Leave Traditional Careers Behind

Kelsey Ogletree, a freelance journalist, didn’t expect to become an entrepreneur when she started hosting a Zoom call for publicists and fellow writers during the pandemic.

At the time, the contributor to publications such as The Wall Street Journal, Travel + Leisure and Robb Report was writing a newsletter letting publicists know what types of sources she needed for her stories. With everyone stuck at home, she decided to see if a handful of her professional friends and contacts were interested in joining a call where they could discuss what was happening in the pandemic and network. That led to an accidental discovery: There was a lot more interest than she anticipated.

“I thought maybe five people would say yes, and I ended up getting over 100 people,” she says.

That call was so well-received that she started to host one every week during the first couple of months of the pandemic. Then it occurred to her that she could turn it into a business—one that offered the independent lifestyle they wanted. That decision began her path to running Pitchcraft, which she bills as a “people-focused PR platform.”

Many people in today’s business environment are worried about their ability to make a living in the future from the skills that have taken them this far. Journalists are often among them. The U.S. Bureau of Labor Statistics projects that jobs for journalists will decline by 3% from 2023 to 2033, shrinking by 1,400. The same economic forces that affect traditional staff jobs in the field also impact freelancers like Ogletree. However, many people do land on their feet as they navigate disruption in the industry, and her story offers insight to how professionals in many fields can use their existing skills to create new revenue streams without leaving their original field altogether.

One thing that gave Ogletree the freedom to start the business was moving from Chicago to less-expensive northwestern Alabama with her husband, Derrick Ogletree, a former senior advisory specialist for Nasdaq. They moved to an apartment above Derrick’s father’s garage, and Derrick began working remotely.

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Living mainly on his salary, they soon set up a Squarespace website for e-commerce. They began offering travel publicists a package of four calls where they could meet writers in the space. Pitchcraft introduced the subscription for $200.

“You would hear from different travel journalists talking about what they were looking for and how to pitch them,” says Kelsey. “We did that for a little while, and I would always sell them out. Then I started hearing people say, ‘I wish I could stay connected with all of the people who show up for these calls.’”

The couple eventually decided to build a paid membership community, focused on journalists and publicists in the lifestyle space—meaning travel, food, home, design, beauty and wellness. They launched it in December 2021, using the platform Kajabi. By May of 2021, Derrick had left his job and joined the business full-time. Needing to customize the community, they built their own platform, with help from a contract developer, launching it in December 2022. One strategy that proved valuable to attracting paying members was offering 15-minute demos on video calls, to make sure prospects could use all of the platform's features from the start.

They are now hosting events such as a monthly discussion with journalists. One recent program featured three broadcast journalists from Good Morning America, Fox, and The Today Show. "We were all talking about how to pitch gift-guide products on national TV,” says Kelsey. “Our members were really eager to get their clients on the radars of these journalists—and the journalists were also saying ‘Give me your best ideas because I get 1,000 emails a week and I'm so overwhelmed.”

As they built the community, they focused on finding members who wanted to not just benefit professionally from the community but also to give back to it and get to know the other members. "We always say we like to build relationships, not lists," says Kelsey.

That approach worked well, and the business now generates revenue in the mid-six figures, according to the couple. It has also allowed them the flexible lifestyle they want to enjoy raising their one-year-old son. “We’re able to take him to school together and pick him up in the early afternoon,” says Kelsey. “We’re both always there for him when he gets home.”

With the field of journalism in transition, Kelsey sees hope in her story for other journalists who might have dormant talents as self-employed entrepreneurs.

“If I hear of a journalist getting laid off, I know everyone tends to say ‘Oh, I'm so sorry that happened to you’—but now is your time to think about what you do better than anybody else,” she says.