Podcasting pays: OR grad tackles student loans with business

Feb 24, 2021

School loans can be a burden that students carry for years, but Old Rochester Regional High School graduate Trevor Oldham made short work of his by starting a business.

His business, Podcasting You, books financial and entrepreneurial experts and professionals on podcasts. 

In just one year, Oldham was able to pay off the $90,000 debt he had graduating from UMass Dartmouth in 2019. 

The business books people on either 10 or 20 podcasts, analyzing target audiences and taking care of logistics for clients. 

“We do all the legwork for them,” Oldham said. 

According to Oldham, the venture began when he was doing freelance work while he was a student at UMass Dartmouth. For a while, he was taking in all manner of work like freelance editing and writing for blog posts. 

But eventually, he found that his time “was just much better spent” booking people on podcasts, charging around $50 an hour.

Initially, Oldham thought it would take him around five years to pay off his student loans. But by the time his business reached its second year, he was able to hire a part-time employee and Podcasting You kept growing from there. 

Oldham said that whenever his clientele grew, he “would just go out and hire somebody else.” 

And with a completely decentralized and remote operation, Oldham has been able to hire employees across the country. 

Clients of Podcasting You stretch far and wide too, with some of Oldham’s clientele coming from as far as the U.K. 

By focusing primarily on personalities who can afford to pay up to $5,000 to be booked on 20 podcasts, he was able to carve out a lucrative niche. 

And with few competitors and the cancellation of public speaking engagements due to the pandemic, business has been booming. 

“I think we have a competitive edge by focusing on these niches,” Oldham said. 

Oldham and his team put together personalized pitches to get their clients on podcasts, and he said Podcasting You treats its clientele like “sort of an extension of our team.”

As many as 75% of Oldham’s clients come back to be booked on more podcasts, too. Oldham said that the people who don’t come back are usually looking to do one-time media runs, like book promotion. 

“We get phenomenal feedback from these podcast hosts,” he said. 

Now, Oldham said the team has been able to form relationships with bigger and bigger podcasts. 

“We typically don’t try to book our clients on podcasts that have only been out for a month,” Oldham said. 

One of the largest podcasts Oldham’s business has been able to book a client on is “The Art of Charm” which has around 14,000 reviews on iTunes. 

And those relationships with podcasts have come in handy, as Oldham uses his model to book himself on about two podcasts a week.