This transcript was generated from the episode audio and may contain minor errors.
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When a college student starts booking guests on podcasts, he graduates as the owner of a company, paying off his student loans in the process. Hey, what's up? Welcome to Side Hustle School. My name is Chris Guillebeau. I have the privilege of being your host, bringing you different stories, case studies, tips, questions, and answers.
We're gonna talk today about how this business works, how it gets started, where the idea comes from, how he makes it happen, what is the whole business of booking talent on TV, media, and now, of course, podcasts. Well, as somebody who records a podcast every day, and as I have been doing for the past 1,512 days in a row, now 13, I was curious to learn about the other side of things, and I also have some thoughts on best practices. So for anybody who wants to get into this, I'll give you a couple quick little tips. We'll talk about all of it in a short amount of time. The story is called "Dorm Room Side Hustle Grows Into Full Agency." Quick message from our sponsor, and then that story.
[Music]
You know those cartoons where the character is running down a hill, while what started as a tiny snowball rolls after him, growing bigger and bigger as it picks up steam? The snowball grows of its own accord, helped along only by gravity. Now, leaving aside the part at the end, where the character ends up smooshed inside the giant snowball, arms and legs akimbo, a lot of side hustles have a similar trajectory. What starts as a small snowball can take on a life of its own, becoming less side hustle and more, well, main hustle. The story I'm gonna tell you here today, Trevor Oldham, it's just like that.
Born of a desire for a job in college that allowed him to be his own boss, Trevor's side hustle, podcasting you, graduated to become his full-time job. He rolled that snowball down a hill and found himself at the bottom, owner of a small business that books podcast guests and now brings in upwards of $15,000 a month. So what's it about? Well, have you ever wondered how all those talking heads get on TV to promote their books or give their take on a day's news, talk about the stock market, whatever it is, a lot of them use booking agents. People whose sole job it is, is to get their clients a slot on a talk show or a radio program, or yes, a podcast.
In fact, increasingly a podcast. In 2017, Trevor was a junior in college and had begun looking for side gigs on Upwork, a freelancing platform. He applied to projects that played to his strengths, namely blog writing and podcast editing. He had started a podcast of his own during his freshman year and realized he could help other people edit theirs as well. One day he came across a listing from a real estate investor in Los Angeles.
She was looking for help getting booked as a guest on podcasts as a way to promote her services. Trevor had booked guests for his own podcast, so he figured he could easily do the reverse. He began to find more clients who needed this help, fielding calls in his dorm room in between classes. In fact, his clients at the time may not have realized how young Trevor actually was. And pretty quickly he learned that booking guests was more lucrative and less time consuming than the editing work he was trying.
And podcasting you was born. The initial investment was less expensive than a dorm room meal of instant ramen. He had no website, no inventory and no employees. He spent time looking for clients on Upwork, but in terms of money, he spent exactly $0. But today, as I mentioned, podcasting you brings in upwards of $15,000 in revenue each month.
How did he get there? Well, once it was working, Trevor hired a virtual assistant for $400 a month. She in turn brings in around $10,000 in revenue just through cold emailing. They charge a flat $500 for a basic service and up to $3,000 for a more advanced service. While Trevor's initial clients came from him searching Upwork, he began to get referrals over time.
And now gets most of those clients through that cold email. Podcasting you targets guests who have already been on a podcast, emails them to ask if they'd like to continue getting booked on others. But let's be real, has it all been easy? Nope, some things have been difficult. Trevor had to overcome a couple of initial challenges as he sought to quickly grow podcasting you.
He struggled with getting quality clients, first of all, until he decided to start charging more for his service. He also had issues with cashflow early on. He solved this problem by requiring clients to pay upfront. Soon he had a solid track record of previous bookings to back him up. Trevor also dealt with something that's very common, self-doubt, yep, that's right.
He was thinking he was perhaps too young to be striking out on his own, but through working hard for his clients, he was able to banish those thoughts, prove to himself and others that he could do it. Today, the business has booked guests on podcasts such as For the Love of Money, Habit-Based Lifestyle, and Startup Stories. The money the company brings in allowed Trevor to hire three booking agents in addition to himself and pay off more than $90,000 in student loans. [Music]
All right, so I was thinking about this a bit as I worked on the notes for this episode because one of my pet peeves is every single day I get at least a dozen pitches from various agencies who want their client to be a guest on Side Hustle School. At least a dozen, it's often two or three dozen.
I've tried to filter them out in my inbox, but they still come, then I feel bad 'cause I haven't gotten back to everybody who's sending me real email. But of course, they're pitching to be a guest on Side Hustle School, and we don't have guests. And anybody who knows anything at all about the show knows that, but inevitably these emails are like, oh, I'm such a big fan, I listen all the time, and my client would be really great. And so I'm very resistant to that kind of process. Obviously, this podcast is different from so many others.
But still, I think if I'm getting this many pitches a day, I bet bigger shows or shows that are known for interviews are probably getting so many more, right? So how do you be successful in a world like that? I think what you do is you think through the motivations and desires that each party in this process has. Because yes, some podcasts are looking for guests and some guests are up and coming and they want to do the right interviews and all that kind of stuff. So it's helpful to think, okay, what would be the wrong way to do it, right?
What's the wrong way to do this, whether it's this topic or something else, and then don't do that, right? The idea is to think what's the wrong way and then not do that. In this case, the wrong way would be to blindly pitch everyone. The wrong way would be to write to shows like Side Hustle School or others that are really off topic or are not clearly a good fit just because you're trying to write to everybody. You know, the right way would be to really think about how you are being helpful and adding value and just go slow.
I would say also be willing to take some time in building relationships with podcasters and their teams. Sometimes on the podcast end, there's a producer or somebody who's coordinating those bookings. So the right way would be to just kind of build real relationships so that then that person actually wants to get your email, not just blindly email everyone. So my two cents there, but obviously congratulations to Trevor. My favorite part is like paying off the $90,000 in student loans, way to go.
Congratulations, man. And listeners, inspiration is good, but inspiration with action is so much better. Today's show notes, including links to everything I mentioned in the episode will be at sidehustleschool.com/15131513. If you've got a comment or question, just come to sidehustleschool.com/questions. And wherever you are, wherever you go, I hope you'll come back tomorrow.
My name is Chris Guillebeau, this is Side Hustle School. [Music]
