Visionaries Podcast

From Freelancer to Multi-Millionaire Business Owner with Caitlin Pyle

Caitlyn Pyle

Caitlin is a former freelancer turned multimillion-dollar business owner.

In 2014 she started her first blog, Proofread Anywhere, which has since grown into multiple brands and products and is now part of her media company, BCP Media. In May 2017, Caitlin and her husband Ben officially achieved millionaire status — this means they’ve saved up more than one million dollars in assets.

Today's Guest

Caitlyn Pyle


I've got a new show for you today I've got someone pretty special for the name is Caitlin tile

welcome to the content supply podcast I'm Dallin need and each episode we bring you an inspiring brand creator or message to help you discover how you can experience success in your business as we unpack stories and strategies about all things content and growing a successful brand so this is just a hole discovery process for all of us we feature a variety different brands on the show from entrepreneurs entertainers copywriters marketers coaches athletes to designers filmmakers photographers and many more all brand owners all creators so it's my belief as with many others that every company is a Content company and has to be one to stay relevant and competitive because let's be honest the Internet is so full of brands that it can be very easy to get lost in the crowd so quality and effective content really separates you that's why content supply was created to supply brands with ongoing custom content so they can engage with their customers by providing value telling stories and making more sales and when we say content I'm talking about video and audio and written or image all and everything in between all those content creation and building a business is really hard you never finish the building and creating even after you experience some success you have to keep going on in the journey content supply was created to be resource a community and a solution to fill that large gap of content so thanks for joining the show and now let's get to the interview Caitlyn is a former freelancer turned multi-million dollar business owner in 2014 she started her first blog Freed's anywhere which has since grown into multiple brands and products and is now part of her media company BCP media in May 2017 Caitlin and her husband been officially achieved millionaire status one of her favorite things to do is write for the first few years of her entrepreneur life she boxed herself in and wrote almost exclusively about proofreading and freelancing because she believed that's all people wanted from her now she's coming out of her shell to write about loads of other stuff mindset fitness overcoming fear and doubt success making and saving and spending money and building an online business her goal is to inspire you kick you swiftly in the pants on occasion and encourage you to design a life you love one email at a time so Caitlyn thank you so much for coming on the show today yeah thanks for having me so give me a quick story overview and why you decided to build a brand for yourself well I didn't start out wanting to build a brand necessarily I was working as a freelance proofreader which is something I've been doing since 2007 in some capacity but I'd really amped it up as a side hustle in 2009 when I started working and a court reporting office in Orlando and I figured out that you know proofreaders are a necessity for the spoken word when it's you know in a lawsuit of some kind and so yeah I started getting a few clients on this I was working my regular it was an 8 to 5 job and at the time I didn't even know that I could make a full-time income from a side hustle I didn't even realize that I could generate income not from a regular job because that's not what you learned in college you know you go to college thinking you're gonna get a regular job and climb a corporate ladder and that's just but that's the old American Dream that's what it was back in 50 60 70 s 80s and 90s it's like you go to college and you get a job that's the way it works and so I was all set to go and then I was like oh yeah well when I'm 27 28 29 I was I think I got my first job at 22 that job yeah and then I was like okay well we're careful like eight or nine years and then and then I'll quit and have a family like that was the dream you know I think and then about a year or so into that job I started to really really shake it and not feel I felt like the policies of you know if you're done with your work you have to go and do somebody else's work and all that stuff I just thought it was complete BS I'm like this is the most ridiculous thing ever why am i spending nine hours of my day here and why am I only allowed I couldn't even clock out at 4:59 I couldn't clock in at 8:01 like they were just micromanaging me and I wasn't making a lot of money at the time I first started it was twelve dollars an hour and then I grew and eventually got to sixteen dollars an hour and they acted like that was some huge favor because you know they're hiring college students at $12 an hour you know a four-year degrees and whatever and they it was just a really bad place to work and I eventually got fired this August 2011 I got fired and I just I had already put on my notice and it's because I was breaking the rules I was like really just trying I should just quit and I admit that I was wrong I deserve to get fired and you know but the way that they fired me it was threats it was you know slander telling people that I got fired for stealing and their mind was like oh you weren't you know working every hour you're here so you're stealing company time and so they would tell people I was stealing I wanted to go be a personal trainer so my boss told me that I would never become a personal trainer because my foot was too big and that I was a horrible person that I would die alone I had just gotten married and she told me that I shouldn't have children and that she felt sorry for my husband and just horrible things and then she she convinced me that what I had done was a crime and that if I didn't pay her $2,000 that I would get all kinds of trouble and I was just so naive oh that's so toxic so toxic and I didn't know I knew that she wasn't the best person but I didn't know just how not good that she was until that happens and I got a few harassing emails after that in response to on a heartfelt apology because I knew that what I had done was wrong and that I just was too afraid to quit I think not every you said you got a job but know me to do what and when and you just had so much fear around the next chapter of your life and this woman is literally the same age as my mom and there was like 24 years old newly married you know my first job and they're treating me like garbage and it's just not a good example to said no matter what the person is not wrong yeah and I did not commit a crime if anything they committed a crime I talked to an employment attorney and I like now you could totally through them for extortion or something like that and but I just want to be done with it and so at that point you know I did get a personal training school I spent $7,000 on personal training school I did become a personal trainer I did it for three years but I did find that I liked the independence of working for myself more so I had my proofreading clients and eventually I built that into more I got one look like an agency that had a lot more possibility for work and so I just started working more with them and my business grew and I just kept saying yes to the work that would come my way and before I knew it my perfect income was higher than my personal training income and then people would start asking me how home and and so I would teach them and then that's where the idea to actually create a blog came about but at the time I didn't know that you know that I was bloggers or even when I launched my online course and I made like my first ten thousand dollars which only took a few weeks to get to that point I didn't know that what I was doing was called blogging and I didn't know that I was creating a brand I didn't know that I was becoming an influencer or anything like that but we ended up generating with knie where the course launched in February 2015 and within less than 90 days we had done 100k in revenue with that brand and to date we've done more than three million three million dollars another incredible and that's proof read anywhere yeah that's preferred anywhere and on top of proofread any where it's grown you know we're media company now and I run BCP media Ben and Caitlin pile media basically and we have investment projects as well so we've invested in the creator of transfer of anywhere to help grow her brand we've invested in scope school comets well and we've invested and fitness personality who's the chemical record of number of pull-ups in a minute Michael effort he's he can do 50 pull-ups in a minute and you're working on beating his own record at the moment but we were confessor than him as well just to grow we we just create content that sells like we create content that adds value to people's lives work at home schools our latest project and so it's just kind of snowballed like I started with just the proofreading skill and then I just did something with that and then just when opportunities came my way I just answered the door you know even though I'd been in the habit of saying somebody gets that whenever opportunity would knock I'd be like all right somebody else will do it you know but I didn't start out to answer your question it seems like a long story but answer question I didn't start out with the intention of creating a brand at all it just kind of evolved that way and I like it actually I really like it wow it's incredible to to learn of that success that came from the time of struggle - because you weren't I mean you said you weren't necessarily looking to create a brand so to speak but it just evolved on that snowball than that I think it's because you I think it's because you jumped on the opportunities that you saw and do you how else did you basically leverage tools or resources exist online whether that be different course building tools or sells funnel practices what what different tools did you use to help bring in that first 100k or that first 10k well it's very basic it was very vague thing it was nothing fancy nothing that cost a lot of money I think the whole first rendition of my course cost less than $500 or at least less than $600 I used like the least expensive options I didn't use teachable or think if ik and I think those platforms are great but I was I didn't have the best mindset and that's really I didn't think of it as like an investment I thought of it as like oh spending this money I just have a completely different mindset and what I was doing then as I do now and so I was hesitant to spend money on stuff because I didn't give it an investment I was convinced that you know this is probably gonna be just a little side hustle that maybe I get an extra $5 a month from a few students or whatever and I didn't expect for it to grow to where it did and so I bootstrapped a lot of it and I started with just a premium wordpress plugin that cost me I think $97 or is like $87 so they found a coupon for it online and then MailChimp and I set up like a seven-day autoresponder which in my mind was like that's a sales funnel you know and it really was cuz it worked it basically just took somebody from very curious and then eventually led them to the sales page was got me to sales so it was a very rudimentary form of a sales funnel in the form of like a free intro force to was a concerning that I was doing and yeah I didn't do a lot of video I even the course was largely text because I was teaching proofreading but I did have some videos about like grammar lessons and stuff like that and I didn't influence her outreach which I laugh at that now at the time because I didn't at the time I didn't think of it as influence or outreach I was just like networking with affiliate marketers you know I would find that would type in proofreading and see who was blogging about it and then contact that blogger and say hey I had this course do you want to interview me on your site and then I'll give you I think it was like 75 dollars per sign up or whatever and then so I got a few people that said yes and you know that they were pretty much my level now or you know a few years into their own blogging career and you know they didn't ask me PC was so just like yeah I think my audience will like that else I'll try it out you know you're gonna be creating the content I was the one answer the question that basically would create a piece of content for them they would post it and then they've done almost no work but because they have their audience and it's just really passive and so I just needed a no brainer for them it really just worked with the network that I created it was a little scary at first as my they say no but it was something unique that they weren't offering already and so it was kind of a no-brainer for them like yeah you know I'll check it out and some people did say no and some people are like yes but then they never follow it up and so some people are better our blogging than others to pull the little nuggets from what you said it sounds like it's it's not necessarily the tools that are the solution it's ultimately if the value of the product that you offered and I think just by reaching out there people that you reached out to initially the affiliates or the influencers is they pretty quickly saw either the value proposition you provided or just the ability to help provide additional value to their community already and it wasn't just it wasn't rocket science it was more of just I'm Caitlin and I have an incredible product to sell and because people saw that pretty easily it sounded like their response was really positive yeah it was not I wouldn't say that anybody could do it because I consider myself an exceptional writer and so I can make a pitch to somebody and be really clear and what the what doctor is why they should promote it and then kind of give them social proof and so I would reach out to a bigger vlogger after I reached out to a smaller blogger and save someone so it's already on board and in the last week has generated X number commissions so I even though I didn't have like the fancy UPC numbers or anything huge I would just you know drop some names on who its promoting or send them links to you know an example of an interview that I could do for them and I'm really grateful to those initial few people who who turned gamble it was really a gamble because I had no proof other than you know my own blog and testimonials but I had no proof that my product would sell for their audience and they took a risk and even even if it was a small risk to them it paid off for them and for me so yeah it's definitely I think about those relationships it's a relationship economy with content you know you use your content to build relationships and that was basically what me posting I call it trust by proxy and so I would create content in the form of an interview for these bloggers and their audience would say oh you know it's so-and-so is promoting or introducing me to their friend right and so I would gain trust of their audience because I was on their blog and it's so much more effective than me just coming on as a guest it's more effective than me just doing a guest post where I talk about proofreading event pitch my course and so interviews just allow the at least give the appearance that the blogger is the one like in charge and not her or him just handing over the reins to some marketer and yeah that's why I like interviews way more than guest posts where I just like write content and then pitch product I don't like doing that I'll do it but and I think the interview whether it be podcast video written it gives the ability to provide a little bit more of that I guess supportive or that relationship aspect of marketing because it's those on you know kind of like we're doing on right those on both the giving and receiving side are getting benefit of experience of like this is to provide value for a community I'm looking to build around those who are looking to learn more the know-how behind content creation or building a brand but also for your side is you're looking to reach out to those who are interested and learning how to improve their proofreading and their copywriting skills or now more recently your work at home school experience and that ability to live and to work at home and have more of that financial freedom for yourself and your family you know how did your husband get involved now that you guys creates BCP media yeah DCP Ben Kalin Pyle media well he was working a job that he hated he was a financial aid at a private university for private university so I like to call that was the original information products where people pay a ridiculous amount of money to go to the school that he was working at like they would come up with like a hundred thousand dollars in debt for like a two-year program like a tech film making video game graphic that kind of school really really really expensive program and he was in charge of getting financial aid for them basically setting up their their ball and chain for the rest of her life so I actually unfortunately it was just like draining him and so he was really unhappy there and had started a listen to podcast and had heard several different interview with entrepreneurs that were living the life that were not living basically with our own products and our presence online and selling things that were valuable to people and solving people's problems and he was just really inspired by that and so he started to get into entrepreneurship and how to build a business and join a program called the foundation which was basically he learned how to build a software business and in it getting introduced into that community even though he didn't come out with a software himself we ended up with proofread anywhere basically because he was sharing things about online business with me and so I learned through osmosis I was very skeptical of like I don't like those online marketers they are plenty there they're just not people I want to be associated with I had been targeted by just marketing I think anybody who says they don't like marketing just has been targeted by a lot of bad marketing and so now I know that and I keep that in mind when I market on my camera and be like all those marketers because doing your own way it's just being yourself it's super authentic and that's what draw draws you're your ideal audience you is the people that speak your language basically and you have to be willing to speak that language and not trying to speak the same language a real speaking people know that it's kind of like short-term and long-term gain I think those who are more those slimy type they're looking for the short-term quote unquote success really you know that the quick financial gains versus if you want to build something long-term you have to put stock in the relationships and the authenticity yeah and not just let that be lip service as well or like so-and-so is saying this and got this or sold so I can say they have to get the same result no like you might get some short-term results but if you can't deliver and if people sign up for whatever you're offering and they're just like you don't know what you're talking about you know it's gonna show and so you might be able to get some short-term gains like that way cheating your way to success but then it's not any long-term because it's it takes a lot more effort to to really build a business and it does to just like well I should say it takes it actually takes more effort to fake it than it does to make it and so a lot of people they owe you you make it but no if you actually take the time to make it then instead of trying to fake it the whole way copy other people and not really learn the skills he needs to do we were trying to do then it just doesn't come out in the end so yeah so Ben would just like put bugs in my ear on stuff and then finally one day it was November 2014 I was like alright I'm gonna buy a domain and that's when I bought preferred anywhere in November 1st 2014 and within 10 days I had my eBook up for sale I was just like putting it was just like my Minimum Viable Product didn't know that's what it was called at the time just everything I thought somebody need to know to be able to do what I did and we sold like 17 copies of the book and were like the one-on-one training program and from there we were able to create an online course but when I launched the book I had no intentions of making anything more than a book I thought it would just be like an extra seven hundred hours a month or something you know max from the amount of people that I can train every month when I won I had no idea how to scale it and see what online course I just thought you can't teach proofreading online and all this stuff I had all these like mental blocks but because of Ben's involvement he was able to show me other people were teaching skills online and so I just thought about him like how could I I could you know use a screencast software plug it in my iPad and you know do an annotated video or I show people how to use tools and I just came up with the ideas and put it all together and so of course and yeah so we didn't create software but that's basically how Ben was involved that was the original question was like he he kind of pushed me into getting started and showing me the possibilities and honestly listening to the stories of the people that I made $100,000 and three months which is what we ended up doing anyway the the stories they they turned me up I'm like that's that's a pipe dream that'll never happen for me but it wasn't until he said that somebody he personally knew and one of his like small group masterminds I had made like twelve hundred dollars in a month I'm like alright that sounds more realistic it could be really cool or maybe it was like thirty I would think it was thirty five hundred dollars which was about the average amount of income I made as a freelance proofreader I'm like I can make that much selling an online course I wouldn't have to prove it anymore so that was kind of like my goal is to replace my proofreading income with pass it more passive I can't call it pass it by any means but with a more passive not exchanging time for money like directly something that I could earn where I wasn't you know spending the time doing a work kind of thing yeah yeah definitely did you have an existing email list in community that already built up by the time you launched or were you did you kind of kick start this course and then start to build your audience after starting in that course we had a small list of people that I knew when just from starting the the ebook and it's like my crappy WordPress site was up and somehow people were finding it and I was in different Facebook groups and would would occasionally just write about it I went one on Fiverr this was like shady marketing but I did not I literally did not know any better I went on Fiverr and found proofreaders offering her services for next to nothing and I was like do you want to learn a better way and I asked him enjoying my newsletter and so through that like just totally manual marketing I was able to build a little bit of email list I posted some ad signed craigslist that got me got flagged like every single time and it was crazy because people thought that I was offering a job but I wasn't and I was very clear and they add that people would click over and be like oh they want you they want she wants to train me not give me money right so I would I would have been met with a lot of skepticism because I was marketing to only proof readers that were already proof readers right but I still got my first few clients doing that and then when we launched the cord so that was a book one last the course I had about two hundred twenty people on the email list and we sold to eighteen people that week which ended up being just under $4,000 a revenue so that was already pretty cool I've made that in a week and that was the original goal is to do that in a month it was really exciting but then from there branching out with building through affiliates and just getting more exposure on other people's blogs doing interviews and guest posts mostly interviews and that kind of thing that's how I grew my list cuz I would just be a guest on like I was on the penny hoarder before the penny quarter got super big and so I met Kyle the owner of penny hoarder when he was still answer his own emails basically and was able to be featured on his website and I got tons of traffic money-saving moms a big blogger send a lot of traffic so I got people into my my rudimentary sales funnel that way and grew my list that way and paid affiliates that way and I think just working with other people is critical especially you know just starting out because even somebody with like a list of 2,000 could send you some people because there's so many affiliate marketers I want to make money telling other people's products they don't have their own products but if you have a product then they can market it as as almost as if it was their own product basically and just collaborating your not being afraid to step out I think it's just so key it's people look at other bloggers and look at them as like competition but in reality we're teammates and there is we're all different we all offer something of value unless and I know there's people out there that do this unless you're literally ripping off somebody else's product we all have something unique to offer and so we can see past the similarities and look at the fact that we all speak slightly different languages or vastly different languages in some cases and we can all offer something of value to our audience so I started offering Affiliate I just start doing affiliate marketing in August of 2015 so about six months or so after we launched the course somebody approached me and asked me ask to promote a bookkeeping course and I was like my audience will hate that you know I was really skeptical and like why would I promote something that's not proofreading I couldn't wrap my mind around it then I was like because not everybody on my list is an ideal fit for my product most people don't make that connection and they're just like I'm talking about cooking I could only blog about cooking it's a Oh like with the work at home school you were trying to break that mindset of like no you're probably good 50% of your list once the work from home and so you can promote something like that that's really gonna add value to their lives and add money into your pocket affiliate marketer so just kind of helping people collaborate instead of looking and you know living in this little box of a blog thinking that they they can't break out of that if I can break out of the proofreading box and start marketing all kinds of stuff to my audience and I think that anybody can and I think it's evidence - of what you've been able to build with your husband is it goes beyond just you now you guys have this shared company BCP media which has then evolved proofread anywhere you get another one it was proof you done it anywhere and transcript anywhere schoolbus cool calm and then now working on working on school so you already kind of talked about how everything evolved into work at home school tell us more about it what is included in the course what are the benefits what is kind of the I guess the you can't call a promise to outcome but but what's kind of the results that you're hoping people will experience yeah well the unique thing about working on in school is that it's not just a program I didn't create all the content a lot of my content is included and work at home school but it's a collaborative project and so we're bringing in instructors that already have proven results and we're bringing in their content as contributors and instructors and work at home school and so we're leading into the launch of work at home school with the working on summit and so all the speakers and we're going on summit are the contributors working on school and so instead of just bringing on a bunch of people to promote of products that I'm selling that only I'm going to benefit from we're bringing on people to promote everybody's project and everybody's content and helping a lot of people in the process because our contributors have a lot of amazing skills that they're sharing with the work well you know and what's unique also about working on school is that it's not just the content that's gonna give you the skills it's all the stuff that's in addition to that so it's the mindset it's Fitness focus time management Civet II it's all those things that we struggle with and creating work at home lifestyle all under one roof with proven experts to help in every area and so there's there's going to be something there is something for everybody and so there's three different levels and you can progress through the levels as you can create your own payment plan in that way starting with the curious level moving up to the confident level is moving up to the committed level which is the top level that includes all the content from our contributors well I think we're gonna old school is kind of like my debut out of out of being like a small small-time proofreading blogger so for forever I've just been like the proofreading girl you know and some people kind of assume that I don't know internet marketing that I don't know as much as them if they've been blogging for ten years or if there have been an affiliate marketing for longer than me or whatever but I'm a really fast learner and I have been fortunate to have the capital now with you know the basic media brands that I can invest a lot of money into building something huge launching year that's gonna help a lot of people like working on school or investing over $100,000 to build it and we're gonna launch it and if people don't know who I am now or think that oh she's just some dumb little blogger who blogged about proofreading like how much money could that make they're gonna know who I am but anybody who's rejected me like in the past for you know collaboration like we're approaching a lot of people to contribute and to speak in the summit everything and you know some people are just you know rejecting that opportunity thinking that is how can be worth anything and I think they'll be sorry because it's gonna be amazing and I am there's no reason why it can't be amazing because we're investing a lot in it and we're bringing you together I'm gonna blow your mind the work at home and then we're gonna one world to help a lot of people succeed and nobody ever became poor by giving and so we're just gonna be giving and giving and giving and just watching that multiply I think and it's gonna be amazing I can't wait man that's awesome that's super exciting so where can people find you online well probably like the most central hub there's be UCP media inc dot-com and that's kind of my all-in-one hub for people that want to learn about the courses that I create and then also if you're an affiliate that you want to market work at home school or preferred anywhere or transfer anywhere you go to be CVT and there's a link for both so you can learn more about the product or the brand or you can learn about how to promote that product and so these community comm is the best way to find about everything that we do all the content that were either creators or investors and Kalyn pile Co Co is where you can sign up for my email list and I send out three emails a week that people just rave about they love my emails and so I I yeah if you want to sign up for those emails it's cool yeah at Facebook I'm on face a lot so just look okay to file you can find me awesome and as you said to you're a very talented copywriter and now obviously a big growing constantly growing brand owner what what's kind of some parting advice for someone just starting out where does someone begin if they want to build a work at home brand yeah that is a that's a good question so I would say that don't let the the idea that you don't know how to do something be the reason you don't learn how to do that thing so I looked back to November 2014 and I was saying I don't know how to build a website you know if I let that continue to stop me I've been saying that for months because I had thought my husband and he's kind of putting things in my mind for quite some time since he had started his unfinished program about getting something going and I would always say well I don't know how to start a website like then it would just stop there I'd be like okay well I guess I'm not doing it you know and so I would come up with I don't know this I don't know that and use that as a good excuse and I didn't know that that's what it was at the time I just thought that's the fact of life I don't know how so I can't you know and I think a lot of people do that especially if they're new and they see they'll see this in here maybe like I'm never gonna be where she was well that's why I love to talk about where where I started so much because I'm never gonna forget that and every time I start a new project now even when I was first started working on schools I don't know how to do that and you find people who do and you learn from that that's all you have to do and you've got skills and that's what working on school is about as you build skills and you earn more money that's all there is to it so not let don't let I don't know how stay in your way and know that if you want to make more money you just have to learn more skills and that might be marketing skills it might be a skill that you offer to people that they need that I'll solve a problem for them but it's just I say most skills is momoney well kaylynn seriously I've learned a lot just in this quick conversation with you and I can see why people have paid so much money over all these year you know it's been three plus years almost yeah as you and Ben are building up you know this Empire of a business so I'm super excited to see where you'll go from here especially now with the start of work at home school which does appeal to an even wider audience beyond just proofreading and copy so I'm super excited to see what happens and I appreciate that you you hopped on and join me in this conversation it's podcast thanks yeah thank you I'm excited to see where you go as well and I know our paths will continue to cross mm-hm for sure so we mentioned content and brand building throughout this episode so if you're overwhelmed with running your business and you know you need more content especially an ongoing constant supply of content that's custom all in order to take your brand to the next level then make sure to learn more and check out our website of content supply at content supply dot IO so thanks for listening everyone and we'll see you on the next episode


Dallin Nead

Dallin believes in putting family and God first.

He's the Chief Vision Officer of Content Supply, Advisor to multiple startups, serial entrepreneur and an award-winning producer.

He helps brands create authentic, results-driven media so they can share their message and vision with the world.

He helps brands clarify, create, and communicate their vision for a happier, more meaningful life, business, and community.

He consults with small and large companies including Princess Cruises, U.S. Marine Corp, Teachable and many others.


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