25: How Trevor Transformed from an Overworked Freelancer to a Thriving Agency Owner

Behind Their Success: Ep 25

trevor

Trevor Oldham: [00:00:00] I had that mindset. Because I was a broke college student. I was like, why, how could someone pay 3, 000 for our services? I don't even have 3, 000 in my bank account And looking back, I was like, no client's going to care about how much money all they care about is how good of a job I do for them.

 Welcome to Behind Their Success. This podcast is for people who are feeling stuck on their entrepreneur journey or in their careers. It's for people who want to scale and grow their businesses, learn about the power of mindset, or they just know there's more out there and they want to start making changes.

Paden Squires: I'm Paden Squires, the host of the podcast. I was never cut out to be an employee. And when I was an employee, I was bored out of my mind. So I made a plan. I studied and passed the CPA exam in eight months while working all with the end goal in mind of quitting my job and starting my own business. I did that in 2014 and it has been an amazing wild ride since.

So now let's hear from other entrepreneurs and what mindsets and probably more important, what actions they have taken that have created [00:01:00] and led to their success.

Hello everybody. Welcome back to behind their success podcast. I am Peyton Squires, the host. And today we have Trevor Oldham. Trevor in 2017 created his company podcasting you. The company is a podcasting booking agency that helps investment companies generate more exposure, generate more capital raise and networking opportunities.

They have worked with over 400 individuals and scheduled more than 6, 500 podcast interviews. Trevor, 

tell us, uh, podcasting, you started that, uh, in 2017, tell us a little bit about that company.

Trevor Oldham: Yeah, most certainly. So we help folks primarily like in the real estate investment space. We started branching off to the oil and gas space and you have folks in the laundromat space. We actually work with the client. It's pretty crazy. I never knew it existed until they became a client of ours, but you can invest in barrels of whiskey.

And it's like the minimum investment, like a million bucks to invest in it. It's pretty heavy duty. I don't know if I'd be investing in that asset [00:02:00] class. I don't know enough about it, but yeah, we primarily work with alternative investment companies to go out there and we'll get them booked on podcasts.

We work with corporations that just need guests for their podcasts. Sometimes people need editing. Sometimes people don't need social media content created based on their interviews and what they're doing. So it's sort of like a full service podcast agency, but honestly, I never really. never really expected to be in the podcasting space for this long, nor that I expected to be in the PR space as well.

It sort of just came to fruition and I'm sure we'll get into it, but yeah, that's, that's a little bit of background. Like a company that has been doing it for seven years now, bootstrapped the whole company on my own, you know, never took in a dollar of investment, just started off with me for the first year, brought on someone the second year.

And then now I think we're up to like it. Eight or nine employees as it's sort of grown over the years. 

Paden Squires: So give us a, give us a little more about your background, where'd you come from and kind of how'd you end up kicking off this business? 

Trevor Oldham: I think for me, I just always, always had the entrepreneurial bug from growing up [00:03:00] early on, I was trying to mow people's lawns, just buy and sell baseball cards.

that I can make some money on my own, never knowing that it was called entrepreneurship or, or working for yourself. But I always just had that bug of trying to be an entrepreneur. Fast forward. So now I'm a senior in high school, still have this entrepreneurial bug and long story short, so I ended up buying these phone cases from China.

I bought them through a site called Alibaba. Resold those phone cases. Unfortunately at that time, Alibaba was a little unregulated, so they were all knockoffs. So that didn't last very long. I got shut down pretty quickly on eBay, but that led me to my next company, which was buying and selling bracelets and watches.

And it was through that company. I got to work with a lot of influencers and I already use AliExpress similar to a sister company to Alibaba, where instead of having to buy 50 phone cases at once, I could buy bracelets for a buck. And I could buy watches for 2, sell them for 10, 20 a piece, whatever the pricing had been.

And it was through [00:04:00] that company. I'd grown like an Instagram following of, I don't know, like 10, 000 followers at the peak of the company. And it was more of an e-commerce store, but it really wasn't that exciting to me. It was just an area where I was trying out a different business. Eventually that led me to another company and this is where the podcasting story really starts to begin.

I started a motivational based company with a partner and you could see you go on Instagram, you can see motivational quotes and different things like that. That's what we did back in 2015 and we actually grew our Instagram account to like a hundred thousand followers. We had a pretty successful Facebook following.

But I know we could get shut down at any moment, whether we want to or not. So it was like, how can we build our own audience? So I thought to myself, well, let me go out and start a podcast. So I did start podcasting two years back in 2015, and we were still bootstrapping that company. So I was the one booking all the guests for the show, editing the podcast, creating the social media clips, doing the show notes for the podcast.

Basically everything. That goes into a podcast. And after about [00:05:00] two years of running that company with that partner, it just wasn't working out. The company wasn't making a ton of money and I was going to college at the time, but I was putting in like 40, 50 hour weeks into this company. So it was just like a lot going on.

I honestly just felt as though I was getting burned out from working two years and not making any money, which I think anyone would, would feel the same way. And I just started freelancing out the skills that I have learned when it came to podcasting specifically. And that's really how the. Podcasting you company came to be, I started finding people that wanted to get booked on podcasts, people that need editing for their podcasts.

And then after about a year of doing that, I realized I really like booking people on podcasts more so from a time and money standpoint, where if I'm editing someone's podcast, I might charge them 50 bucks an hour to edit their show. And it's going to take me like an actual hour to edit them. But I can say, I'm going to get you booked on a podcast and you're going to pay me 50 bucks.

Whether I get them, it takes me five minutes to get them booked on a show or it takes me an hour. Usually it'd be [00:06:00] in under an hour. So I realized my time and value money wise made more sense to get people booked on podcasts because I wasn't having to sit there and edit and take more of my time. And. That's really how it started.

I, like I mentioned earlier, one year and I was like, okay, me, I needed to grow this company. I need to bring someone on because it's not going to be going too well. And then I think it was really two or three years. And before I even had a website or anything like that, it was just still picking up freelance clients.

And then people kept asking me, Hey, can I check out your website? I I should probably develop at this point. But it was, again, I was bootstrapping it. I learned how to build a website on Wix, on Squarespace, on WordPress. I think it wasn't until. Two or three years ago, I paid someone like 500 to make our website look a little bit nicer.

And then I think last year I paid someone finally like a couple of thousand to make it look very nice and professional, make sure the speeds were, were fast. So, but I mean, it sort of just grew over time and like anything else, I liked bootstrapping because I always felt that I was in control of the growth where I never grew the company so [00:07:00] fast.

At some point I grew the company too fast. I was taking on too many clients at once, but it was a different revenue model. That we had, but that's sort of a backstory. I mean, I got started in entrepreneurship probably 2013, 2014 at this point. So, you know, being running different businesses, podcasting, you just happened to be the most successful one and then also made the most money.

So it's like, why, why not keep rolling with it? Yeah. So it's kind of 

Paden Squires: interesting. You, you know, you were kind of switched into more of a, like a value type billing, right. You know, when you were doing the editing and doing an hourly type rate. You know, as entrepreneurs move up the scale and move up, you stop trading time for money, right?

Um, where you're, you, you start getting paid based off the value you provide for somebody and not necessarily how long it takes, that is a much better business model, right? 

Trevor Oldham: most certainly. Yeah, no, it's, it's a lot 

Paden Squires: better for sure. So you, you know, you started in 2017, you know, working, working with, starting to book people on podcasts.

What do you think this company kind of takes off compared to the previous ones you, you had tried in the past? 

Trevor Oldham: Yeah, I would say one [00:08:00] more. So I didn't have to spend any money on advertisements. And I found that was sort of a challenge in that these other companies could just never really get it down.

I think the product. Well, one, I could think of the phone case. I was just pretty trying to make money. There was nothing. I've got the bracelet and watches. I just felt, and I just felt like the product wasn't good enough. I'm buying these bracelets and watches and they just felt cheap to me and I knew I was just marking them up so much and.

We had partnered with a charity and we were donating a good percentage of the profits to the charity. But on the other hand, these products are getting made in China, I can't imagine China has the best regulations when it comes to labor. So it was kind of hard just mentally knowing that. And, and I was, again, I was, I was putting a decent amount of work in that company.

It was making a few hundred dollars a month. And then the motivational company, it was, I just learned that it really doesn't matter how many followers that you have. It really only matters how much people are going to buy from you. And like I mentioned, we had like a hundred thousand Instagram followers and we would put out a self development course, a morning routine course, and we would make like a couple hundred bucks in [00:09:00] sales and we were spending, you know, 10 times that on advertising.

When I found podcasting you was when I was picking up these freelance clients, I didn't have to have a website. I didn't even have to have an employee. For the first year. So everything I made outside, whatever fees I'd played the freelance platform, and I was using Upwork and I think that maybe took like 10 or 20 percent of what I make.

But outside of that, I got to pocket everything. I'd have to pay anything on ads. I'd have to pay any employees, no one to help, you know, eventually as I grew the company, you have to, you have to do that. But I think that's what drew me to that model. And really what took the company from in the beginning stages to really more successful today was early on.

We would do a pay as you go model. So we would take, and this is where we sort of got overwhelmed with clients. So we would take on a client. We wouldn't build them anything up front. We would say we would get them booked on a podcast and then we would build them once the podcast went live. Well, sometimes the podcast can go live in two months from now.

It could go live in a month, a week, and that was just more difficult. So it was super [00:10:00] easy to get clients with that business model, but it became a nightmare trying to track down invoices. We would get people booked on podcasts, trying to get them to pay. So after about three or four years of doing that, ripping my hair out, trying to figure out how I can grow the company, then we switched more to a high ticket model where now our packages started to work with us was like 3, 000.

And we required that all upfront, unless a client would say, Hey, can we split that package? But that was very beneficial. So now instead of having a client pay us 150 a podcast, we would build them 10 podcast interviews for 3000 with the option to renew at the end of that. And that just, that really grew our revenue quickly.

But what I learned with that business model and what was kind of challenging is some months we might sign up 10 new clients and we have 30, 000 in revenue. And then the next month we sign up one client and we have 3000 in revenue for that month. So it became very hard. To manage the cash flow aspect of the business.

Cause I never knew how much was going to be coming in and any given month. So [00:11:00] fast forward to thinking of this last year. So January, 2023, now we switched up our revenue model where it's more a recurring revenue model. So we bill our clients either 1400 a month or 1800 a month. We don't have any contracts with them.

So it's just month to month. Usually most people stay on for like six months, a year or longer. You occasionally get the person that cancels after a month, but I found that was just so much easier to manage cash flow and to grow the business. Cause I could go through and I could say like, okay, I know this is how much revenue we have coming in this month.

If I want to try out a new marketing tactic, I know that I can do that. And two, if I ever want to sell the company and I was learning this from my business coach, It's very hard to sell a company when I'm just doing these one off sales because there's nothing to track. There's no real customer lifetime value or now I can show someone if I want to sell the business, Hey, here's how long the average client is with us.

Here's the average lifetime value. And it just makes it easier to sell the company. And, it was definitely tricky early on in the business because when you're signing up two or three, four clients a [00:12:00] month and having a nice little, you know, Stream of income. And all of a sudden you're, you're switching up the business model, but now, you know, it's, it's, it's nice to look at almost a year and a half later now that we switched to that recurring revenue model.

And I wish early on, I would have just done that. That would have saved a lot of time and headaches for me. Yeah. Yeah. I 

Paden Squires: mean, you know, yeah, that subscription type model, right. That is, uh, um, super valuable for a business, super valuable for growing the value of your business. Because it's so easy.

You know, there's, there's just a whole lot more practical information there to value, you know, present value of cash flows and how much you're at, you know, the business, you view it as an asset, you know, how much income can it, you know, it becomes a lot more predictable. So therefore the asset becomes worth, certainly a whole lot more value.

you know, along this way, you've probably learned a lot of different lessons. What would you say is one of the best decisions you've made, in this process? 

Trevor Oldham: So I would say one, and it came from my business coach and, you know, And it's harder when you started your business early on, but I learned where you start to make a decent amount of money in your business, but firing clients that give you a headache.

And I've had clients where [00:13:00] they've called me up and they're just like berating me. Like to give you an example, I had a client call me up and he had to do an intro call with a podcast host. So that basically means it's like a pre-interview where you hop on with the podcast host, you chat for a few minutes and you get to know each other.

And then you, then you schedule your interview at a later date. Okay. And he called me up saying he's never had to have done this. And just like berating me. I'm like, is this really worth to have this client on as a partner? And there's been other clients where they have, we sign them on and then they're just, you know, they want to be CC'd on every email where I feel like I'm being micromanaged, they come on.

And the next thing you know, they say they want to get on the Joe Rogan podcast, so they want a full refund, things like that. And now that like 95, 99 percent of the clients are easy to work with. But you do get that one client on occasion where it's just not an enjoyable process. And I can look at any time our clients, like right now, I think we have like 40 clients or so, like pretty much all of them are good and easy to work with.

I don't think we have anyone that we have any problems with right now, but occasionally when you work with enough [00:14:00] clients, there's going to be one here and there. It's just hard to deal with just their personality. And like what we do is I don't care where we are in the package with the client.

If we're halfway through, if we're a third of the way through, I just refund them the full amount back. And I just find that's the easiest way. Like do you pay this 3000 and we booked you on five shows and you're just being a nightmare to work with. I'm not going to refund you 1500, you know, half of what we did.

I'm just going to refund you the full 3000 and be done with it. Obviously that's not, it's not enjoyable, but for just peace of mind, it's just so. Well worth it. And that was like a big learning curve for me. Cause I don't have the clients that just keep you up at night. They're just always asking for updates.

It's very hard to manage. It's like, it's really not worth this. There's enough people out there that could use our service. Why not just work with the people that I want to work with. And then on these one offs that occasionally happen, just, I'm just going to refund their money and be done with that.

And that seems to be the best. One of the better things that I've learned. That is 

Paden Squires: a lesson I certainly have learned, along my way and, and the hard way [00:15:00] at times, right? You know, I've, I don't know, I've probably worked with over a thousand people. in my businesses doing tax and wealth type stuff.

But, yeah, certainly there's, those people that just for one reason or another, you might not, Click personality wise and like, especially if you've grown your business and got it a little more established, like, you know, when you're starting out, it's like, you'll man, you'll do about anything for a paycheck, right?

It's like, you're just trying to eat and survive. But you pay for that later, right? You take on stuff, you start doing stuff that is really not necessarily in the business model or in the long term plan. or you're willing to deal with people and their problems, getting pushed off you while you're trying to make money. At some point you just gotta cut that stuff loose.

You know, I, I personally like it if, you know, seeing your name on the calendar doesn't give me a great feeling. It's probably best that we find a different, different way to work.

Trevor Oldham: Yep, exactly. And, I would preface that to going off the clients that are a problem to deal with, and then also taking on just any client just to make some money. That was another learning lesson. And for us, it [00:16:00] was, I know I mentioned we work with the alternative investment companies, but we took on at one point, someone came to us like another agency and they needed help.

Getting folks in the cryptocurrency space booked on podcasts and then that we never done that before But when you dangle like seven or eight clients in front of us, we said yes, and then it was like a nightmare I mean we had to end up refunding like 12 grand or something because it was There was a whole different animal.

I was like, maybe we can have success with it. So that was another learning curve just to pile on and make sure you don't just take on any client just to, just to take them. I mean, it's hard to get in the beginning where you just want to have that revenue coming in to grow your business. But as you go and scale it, it is nice to try to be a little bit more selective.

Paden Squires: like, you get in your lane, and you build out your lane, you become known for the, you know, the alternative investment guy or whatever, and like, you get your processes down, and you know that, and you become more efficient, and it's more profitable. And as soon as you step out that line, lane, I'm like, Oh!

I'm going to jump into cryptocurrency or whatever and sure you could do it and you could figure it out It's just not going to be near as profitable as as your other stuff [00:17:00] because you have got that just so down that it's just easy for you right in in your lane. What's one of the big mistakes you've made along the way?

Um something that uh, yeah lesson you learned the hard way or knocked you knocked you down 

Trevor Oldham: Yeah, I would say just being too cheap when it comes to hiring that's been uh You Not so much of an issue now, but just early on again, starting to grow the company, you try to find the cheapest labor, you try to pay minimum wage.

And I found that it was hard and I tried to go like the four hour work week type of role with and hire, you know, outsource everything to the Philippines. And I just could never get that work. And it was just a nightmare for us. So I made sure to only use it. U S employees. And I found that even by going cheap in the U S you pay for what you get.

So over time, I just learned, I'm just going to pay people a fair wage and I want to make sure that they're getting paid what they're worth. And I found that was just a mistake because I mean looking at that, it would just be like a headache where clients would be complaining to us because our team members aren't doing a good job getting them booked on podcasts.

And the next thing I know I'm having [00:18:00] to step in, which is obviously not what I want to be doing, running the company. I want to be focusing on growing and running the company, Helping out the clients get booked on podcasts. I earned my badge. I did that for a long time now. That's why I hire people to do that on our team.

And I found that was just a big one for me. It was just making sure. That one, I pay people what they're worth. And then two, don't just hire anyone early on. It was like, have a conversation. Do you want to join our team? Yep. Okay. Sounds good. Here's when you can start now. And there's a more thorough interview process that we go through and we do a little bit more diving deep into checking them out.

And that was just, that was just something I had to learn. I mean, I never interviewed people before. I never hired people. I never knew what to look for or what that process looked like. But I mean, that comes over time. And sometimes I'll. If a new position opens up, we need to bring someone on for more clients.

And sometimes I'll interview like five or 10 people. I'm like, they're just not a fit for what we're looking to do. I'll just keep moving along where I feel as though in the past, I would just. hire the first person [00:19:00] I talked to. if I could go back again, I would, I would want to spend good.

I'm not like breaking the bank. I'm not paying like anyone, like a hundred bucks an hour, but paying them a little more than minimum wage or a decent amount, more than minimum wage, depending on their experience with our company, and then making sure that I hire correctly and just taking that time to interview them.

Because. There's been instances where one, like I mentioned, we bring someone on and they just do an absolutely terrible job for our clients. and then when you do a terrible job, then the client just leaves. And obviously on a reoccurring model, that hurts a lot more because that's a lot of income.

They could be coming in or we hire someone and this happened and this even happened like a couple of months back where we bring someone on, go through the inner process, they sound great. And I was like, I don't know if I should hire them, but I'm going to bring them on, you know, we, we need the help right now and then introduce them to all the clients.

And then they put in their two weeks notice, like literally like a week after we got them fully trained and introduced them to all the clients. So now we're scrambling to like, and it's hard because it's like, I just introduced you to all [00:20:00] the six clients that you're going to be working for. How can I introduce someone new a week later telling them that you just left?

So it's just things like that. That's not the enjoyable part of running a business where I should just listen to my gut being like, okay, no, maybe I take on some of the work until we hire someone. Maybe I expand the team's hours or see if The team can come on and help out the client, but yeah, that was that learning process of hiring people, firing people, having people on too long, not firing soon enough, where I hate firing people.

It's not an enjoyable process. I think over the years and seven years, maybe fired like three people. And again, it's not enjoyable, but. I should have fired them so much earlier. It would have been way less of a headache for me having them kept on longer, but I was like, maybe we'll get it together this week.

Maybe we'll get it together this month. And it's like, they're never going to get together if they don't get it. You know, usually most people that work with us, they're fully trained to know what to do after a month. If we're going on like six months now and you're still not getting everything, it's [00:21:00] time to let you go. And I just feel bad about firing people. So I think it's just more me, but knowing like it's what's best for the businesses, probably what's 

Paden Squires: best for the employee too, to be honest with you. I mean, you know, it's hard to just say that to them, but it's, you know, it's probably true.

It's like, Hey, this is, this is certainly not working out. You're not getting it or what have you. And, it's important for us to take on the responsibility of like, Hey, it's our job to help them figure it out. Right. Right. resources they need, but at the same time, like you can't, you know, you can't make them figure it out going to, and then it gets to that point, you know, you, you've repeatedly tried to help and then you just got to move on and it's not fun.

I certainly I've done it a few times and it's not, it's yeah, it's not fun. but uh, yeah, it's part of running a business. So what's, um, you know, you, you talked about hiring processes and maybe firing people even faster. What's, um, once one piece of advice you'd give yourself, you know, you're starting, starting from the beginning again, if you could tell yourself one thing, what would it, what would it be?

Trevor Oldham: It would probably [00:22:00] just be to charge more. And I think I just undercut our services for a long time. And I realized over time that we could have just been charging way more. Where in the beginning we were charging maybe like 50 bucks an interview. I know I mentioned that. And then now we're charging our lowest package or our biggest package is probably like 350 bucks, 300 bucks an interview where it's like that's six times what we were charging in the beginning.

If I had been charging 300 an interview back seven years ago versus 50, think about how much bigger the company would have been and how much more money I would have made. That's something that I wish I would have just charged. And it was early on in the beginning. I was like, can my clients even afford this?

Cause I had that mindset. Because I was a broke college student. I was like, why, how could someone pay 3, 000 for our services? I don't even have 3, 000 in my bank account. And looking back, I was like, no client's going to care about how much money I have, all they care about is how good of a job I do for them.

And as long as I do a good job for them, they're happy to pay the price. So I wish I would've just charged more. in the beginning and then also had [00:23:00] that recurring business model as well. That would have been very nice early on from the onset. Just, I mean, I can't even imagine what we'd be like now. We'd probably be a couple million dollar company at this point.

If we would have, if we would have had that recurring business model from the get go. if I could go back, I would have charged more and had that recurring business model. I think that would have made the business easier. Cause I mean, it was definitely tight there for the first couple of years as I started to hire.

Yeah. Just not knowing, okay, I got to bring on a new client this month to make sure that we cover all of our expenses. And when you're in that scenario, it's not a fun place to be in knowing you have to, sell a new client, bring on the mind just to pay your bills. And that's not a spot. Any business owner.

I want to be and if and I just think back there was. I probably did that for a few years until we really changed Our business model now, and I wish I could go back. I would much rather have had a recurring. Yeah, 

Paden Squires: And you know, I've In my industry, you know, I've run a tax practice, for the last 10 years And very similar very very similar [00:24:00] experience on my side, right?

You know, once again I'm from a tiny tiny small rural, Missouri You And to think that somebody would pay me X number of dollars. Like, like, how is that even possible? Because me, you know what I mean? Like I didn't, it's a mindset shift, right? People, people will pay you what you're worth. But at the same time you got to value yourself.

And, I certainly went a whole long time there undercharging and doing all kinds of stuff because I didn't think I was worth it or, I didn't think anybody I knew would be willing or able to pay that kind of like, you know, kind of like what you said there. exactly.

Well, Trevor, um, appreciate you coming on. What is the best way, um, people can get a hold of you? You know, they're interested in your company, kind of interested in the podcasting space. What's the best way they can kind of connect and, uh, interact with you? 

Trevor Oldham: Yeah, most certainly. So they could check out our website, podcasting you.

That's just podcasting. Why are you? com? Or if they just want to get in contact with me personally, they can just feel free to connect with me on LinkedIn and shoot me a message there. I'm always talking to different folks on [00:25:00] LinkedIn. And that's, that's pretty simple. That's just my name. 

Paden Squires: I appreciate you coming on guys. Thanks for listening and we'll see you in the next episode.

Speaker 2: Thank you so much for listening to the podcast. If you found it valuable, please rate review and share it. That is the best way to help us build this and reach more people as we're trying to accomplish our goal of helping creating more healthy, wealthy, and wise entrepreneurs. You can follow us on social media by searching for me, Paden Squires or going to  www.padensquires.com on the website and social media. We're always sharing tips of personal growth and there we can actually interact. I'm looking forward to it. Thanks guys.