Brennan is a freelancer turned agency owner turned author, teacher, and software founder. Over the last 3 years, his work has helped over 25,000 freelancers learn the BUSINESS of freelancing.
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Worst Entrepreneur moment
- Brennan shares his worst Entrepreneurial moment. Was he able to find a silver lining? You betcha!
Entrepreneur AH-HA Moment
- Build a bridge from where your clients are today to where they want to be tomorrow.
What has you FIRED up?
Small Business Resource
- Slack: Brings all your communication together in one place. It’s real-time messaging, archiving and search for modern teams.
Best Business Book
- Predictable Revenue by Aaron Ross
Brennan: You brought the first hot day of the year to Virginia so, yes, I am.
John: Yes! Brennan is a freelancer, turned agency owner, turned author, teacher, and software founder. Over the last three years his work has helped over 25,000 freelancers learn the business of freelancing. Brennan, say, “What’s up?” to Fire Nation and share what’s going on in your world.
Brennan: Hey, what’s up John? What’s up everyone out at Fire Nation? Not too much. I launched my new course last week so I’m kind of now gliding into making sure all the sites working fine and everything else. But, yeah, it’s been pretty awesome.
John: From what I hear in our little pre-interview chat, it hasn’t been that awesome of a winter for you in Virginia.
Brennan: No, the winter sucked. But, spring is happening so I’m happy about that. Yeah, a lot of really interesting business things on the horizon that I’m pretty stoked about.
John: Well, Brennan, that’s why I brought you on. Your name has been abuzz and I’ve really enjoyed everything that I’ve been seeing, tracking, and following. That’s one thing that I really like about you is the transparency, the honesty, the rawness at times, and that’s what I want to get into today. But before all of that jazz, my friend, we do what I call the one minute mindset, which are five insights into your mind. Would you take about a minute to answer each question? The first one being, ideally, what are the first 80 minutes of your day look like?
Brennan: I’m pretty typically like a suburban dad, so it’s usually coffee and breakfast for the kids and wife and then taking the kids to school. But after that it’s all focused on usually writing. So I don’t check my email, I don’t do anything really before noon, just because when I look at my email and I look at everything I need to respond to or do, it just crushes my motivation. So it’s taken a while because I have a lot of customers overseas who are doing stuff while I’m sleeping, and I know there’s stuff waiting for me, but not waking up to email is probably my ideal day.
John: I love how you said that and I thought you were gonna go with “it crushes my soul” because sometimes it can feel like I wake up on a Thursday and if I had gone networking the night before and if it’s 9:00 a.m., the first thing I think of, “Oh, the weight of my inbox right now is just crushing.” And this is the first thing I think about. So I hear you.
Brennan: My VA just kind of categorizes everything and has an ASAP folder so I have a sub-inbox and she usually doesn’t start until 11:00 a.m. my time, so it gives me an excuse not to really look at my email.
John: Love that. So, Brennan, what’s your biggest weakness as an entrepreneur?
Brennan: I think my biggest weakness is kind of knowing how to shut down. So as entrepreneurs we all know we should live and breathe – our business is our life for the most part, right? And I can’t help but – let’s say I’m out at a park or something with my kids. I’ll check Twitter and I’ll see people that I look up to, friends of mine who are just producing stuff and I’m always thinking, “I should be out writing a blog post right now,” or, “I should be working on that thing I need to do instead of being with my kids.”
And I know this is wrong. I know I’m gonna look back on my death bed and cherish all the opportunity I had to spend time with my kids. I work from home, I get to hang out with my kids and wife all the time, but it’s hard for me to turn off from the busyness I guess, and that need to always be on that hamster wheel of doing something new.
John: What’s your biggest strength?
Brennan: Strength? This might sound strange but it’s probably gonna be my background in the classics. So, studied a lot of philosophy and literature in school and learning about why, what makes humans tick, what are those philosophical underpinnings that motivate people. That’s probably, by far, benefitted me more than any technical course or anything I’ve taken. Just knowing – psychology has been huge for me.
John: So have you got into stoicism at all?
Brennan: Yeah, I’m a big fan of stoics and love Plato, love Aristotle, it’s great. When they say nothing new is under the sun, it’s so true in that a lot of what you see being reinvented in self-help books and everything nowadays, it’s all just rifts on things that the Greeks wrote about.
John: No, I love it. One of my favorite past interviews of eofire was when I brought Ryan Holiday on to talk about his book The Obstacle is the Way. And he kind of brings that modern view to stoicism with a lot of references. So, Fire Nation, if you’re like Brennan and myself who are just into that kind of stuff, definitely a great book to check out. It’s The Obstacle is the Way. And, Brennan, you have some good habits, we’re gonna talk about those, but what’s a habit that you wish you had?
Brennan: I probably sound like a lot of people when I say I wish I was better at sticking to the health and wellness stuff. I used to be on a three times a week gym kick for a while and then I got sidetracked by a bunch of travel and it just kind of screwed everything up. I’m getting back into it now, but it’s one of those things where, because I work from home and work-life balance is kind of – I’m always in my work place. It’s hard to get out of the house, drive to the gym, do things like that. But if there’s any bad habit of mine, it’s definitely – and I fail a lot, I think, when it comes to sticking with the health stuff.
John: Well, Brennan, let me break it down for you. My friend Krista Stryker has an app called 12 Minute Athlete and it’s 12 minute workouts that you can do every day, three times a week, from basically like a six foot circumference area. So if you have six feet, you can do these workouts and you don’t need to go to the gym. It’s amazing.
Brennan: Is it all resistance training and stuff?
John: It’s resistance, it’s squats, it’s all that stuff and you can do it right there, but it’s full body, too. So definitely check it out.
Brennan: Yeah, I will.
John: So, Brennan, you have a lot of, a lot of cool things going on. I kind of think I know what you’re gonna share here, but this is your interview, your answer. What’s the one thing that you have right now that’s going on that has you most fired up?
Brennan: So, it’s actually something I haven’t publicly announced yet. I guess I’m doing it here. I actually just broke ground on the third edition on my core product, and that is Double Your Freelancing Rate. And it’s funny because I started this three years ago. It was a $29.00 eBook that I pre-sold and I created because I wanted to go to a conference that I couldn’t afford to go to. I didn’t budget for it and my wife was like, “No, we don’t have the funds to do that.” So I told her, “Well, what if I can come up with that?” And this is the first, really, the first training product I ever did, this $29.00 eBook that was all about how to price yourself as a freelancer.
Well, fast forward three years, now it’s a $300.00 course that has actually helped just over 6,000 people learn how to charge more. So it’s definitely blew my mind in terms of wow, the emails I get about, “Hey, you’ve helped me be able to afford to get married sooner” or whatever, right?
John: Or take a honeymoon.
Brennan: Yeah, it’s been crazy. So every year I try to refresh it now, so just gonna be adding a lot more, probably a lot more video this time around. With my last course it was a video course and I kind of ditched the do-it-yourself mentality, that I’ve had to up until now, and I hired a pro videographer and he did amazing work. So I’m gonna try to include a lot more of that, I think.
John: Very cool. Well, what I’d like to do now, Brennan, because you did bring this up is, can you walk us, Fire Nation, through this evolution? Because it’s been quite the evolution with Double Your Freelancing and I really feel like our listeners, who are entrepreneurs, wantrepreneurs, sidepreneurs, freelancers for sure, small business owners, they see what you’ve done over the last three years and hear that you’ve now sold 6,000 copies, not really copies, but I guess we should say access points to Double Your Freelancing Rates. Can you kind of walk us through what it looks like from that point, where it was a $29.00 eBook? What happened the next three years to get you to where you are here, today?
Brennan: It’s actually really funny how it all started. I’m an engineer, right? So I’m a software geek. And I used to think – I wasn’t really that fond of that whole training part of the internet. I started this SaaS product called Planscope and the support tickets I was getting weren’t always about the app. They were about things like, “Can you help me get clients?” Or, “Can you help me learn how to close this proposal? Or write it?” Or whatever else. It’s funny because I started to realize that my job is, even as an app owner, was to help people get better at their business, was to help people build a better consulting business.
And what ended up happening was, my first product, Double Your Freelancing Rate, was a direct response to support tickets that I was getting through my software as a service project management tool. And then from there, people kept asking me about, “Well, it’s great that now I know how to sell people, but how do I find the leads to sell?” So that led to my next product and it’s kind of – from there what I’ve just started doing, to be honest, John, is I just started writing to my list weekly. New articles and a lot of these would have called actions like, “Reply and tell me did this answer a question of yours?” Or “What are you planning on doing as a result of this?”
And I just eventually ended up with this Gmail label of thousands of emails where it’s just dripping with raw pain that people had. And I just felt that where I excelled was either researching or responding to the pain points that my growing audience had. So just a lot of consistent content production is what I’ve done.
John: I really love that alliteration “dripping of raw pain.” To me, that speaks volumes of what we as entrepreneurs need to be on the lookout for. When we have emails and people are sharing with us their problems, their pain points, their obstacles, their challenges, we can take that on to provide solutions for them. Because if they’re sharing these things with us, we’re someone that they know they can trust. So, Brennan, they knew, liked, and trusted you and you listened and then you created this solution for this raw, dripping pain that you just saw was so prevalent in these responses.
Here you are, 6,000 sales later with evolution upon evolution growing into what’s now a $300.00 product. That’s something you can hang your hat on. And Fire Nation, it didn’t happen overnight. But it did happen because of constantly keeping the eyes and ears attuned to that audience that Brennan was growing. And Brennan, we’ve kind of talked about an aha moment in a way, about this light bulb went on for you and you were like, “Boom. This is where I can start and grow from there. I want to make some money and get to a conference.” That’s a great time.
I want to have you now get raw with us and take us to a bad time. What I would actually ask you to do is take us to what you consider your worst entrepreneurial moments and really tell us that story.
Brennan: I was a freelancer, this was about eight years or so ago, I was a freelancer and I started to grow my business. I got more work than I could handle and I started just adding employees. And eventually I got to, at the time eight employees, and we had a business downtown, an office downtown and everything and it was going really, really great. Until I had two invoices outstanding for one client who booked about half of our team. And I called up the client and I said, “By the way, your first invoice is now late.” And he said, “Oh, by the way, Brennan, meant to tell you, we ran out of money so we can’t pay you. But we’re talking to more investors.” And they owed me about $100,000.
So this was not – this guy, me, who got thrown into starting this agency. Everything until then was great. People paid on time, we were getting projects when we needed them, kind of by accident in a way. And it was at this time that I realized, “I have a business now. This isn’t kid stuff anymore. I need to be – I need to run this like a business.” And that was, I’m going to be honest, going up to your team and saying, “By the way, I don’t know if I can make payroll next week,” that’s a hard position to be in. Especially when – they don’t care about the circumstances, right?
That’s not their concern. Their concern is they’re an employee of yours, they should be getting paid bi-weekly and here I am with this $100,000 liability that I’ll never get paid on, and it almost made me want to just quit it all and go back to the relative safe harbor of being an employee.
John: Now, you shared that story and as you were sharing it you kind of made it sound like, in some ways, you had fell into this business, semi-unexpectedly. Like you built this because of this demand that kind of cropped up and next thing you knew, you had this guy just saying, “Oh, yeah, Brennan, by the way…” kind of haphazardly. “I can’t pay you that 100K that we owe you, but if we get some investor money in we’ll make it happen.” Was it really that cavalier? Did he really make it sound that way? Because it seems like you almost blame yourself a little bit for not taking a hard line business stance with that guy and maybe with that business and with all the businesses you were dealing with at that time. Am I reading that correctly?
Brennan: Yeah, I blame myself in that I didn’t set expectations correctly with my clients. One of the things that he said after that was, “Well, you know I’m risking everything on this business. This is my…this start-up is my…I’m risking my house on it.” And I remember telling him, I’m like, “Well, that’s nice, but you have everything to gain and everything to lose. I’m just the vendor. We’re the people building it. We’re the services company. We don’t – we’re not privy to that risk. That’s not our concern.”
And it was just really…it was hard for me because at the time I went into business very naïve. I knew how to build websites. I was very good at doing that, but I really had never learned how to build a proper business that, this is how things work and knowing that everything isn’t always going to be perfect, or whatever else. This is, I guess, my biggest rude awakening in terms of business and it almost sent me running back to getting out of it all.
John: So, Brennan, what I’m really getting here and this is kind of what I’m taking in is that, here you have this guy who’s like, “Brennan, I’m risking it all. You should feel bad for me because I might lose everything. I got my house on this, X, Y, Z.” And then your mentality, which I agree with is, “Listen buddy, you are doing that and yeah, you might lose and then you do lose that. But if you actually win you’re going 100X, you get all the upside to the reward. Whereas me, I’m just a guy that’s gonna get paid for work that I’m providing you so you’re giving me all the risk and none of the upside.” Is that right?
Brennan: That’s exactly it. This wasn’t an equity deal or anything. This was straight-up, this was a cash deal. Yeah, it was just – what I learned in going in, what I learned coming out of this, rather, was how important it is to really set expectations with your clients. Understand this is my role, this is your role and this is how we work together and I really didn’t do that. I went into running a business with that kind of employee mentality. I’m very good technically at doing this, all I need to do is just have other people who can do this with me and we can build something awesome for our clients. And that’s all true, but I didn’t give the business side of the equation enough concern.
John: So Brennan, you’ve built up your reputation on really being the guy when it comes to freelancing and increasing your rates as freelancers. I’ve really been a big fan and proponent of freelancing for a long time now, especially for our listeners, Fire Nation, who are looking to break into it. Your first sidepreneur gig, that first dollar you bring in, a great way to make that happen quickly is through freelancing. And some people are gonna have successful careers as freelancers. They can choose their passion, be great in it, and make good money at it.
So I love the whole idea of freelancing, the freedom it gives you to choose where you work, when you work, what you work on and I know your course Double Your Freelancing Rate is powerful because the 6,000 sales speak for itself. Just take a minute, or two minutes here and take some of that knowledge, distill it down, that you’ve learned and share it with those listeners right here, Fire Nation, who are looking to make that first leap into freelancing, or maybe are freelancing right now. What can you say to us?
Brennan: The biggest take-away from the course, and the biggest take-away, really, from my agency experience was that people do not hire you, they don’t pay for websites, they don’t pay for designs, they don’t pay for whatever it is you technically do. And that’s counter-intuitive, I think, to a lot of us, right? We think we build websites and we go and tell people we’re website…freelance website developers and designers. But at the end of the day, the reason people buy, the reason businesses buy, is they want you to get more customers for them or help them increase their online sales or whatever those goals are, but they don’t always bring it to the table.
So I might think as a business owner well, if I had a new website maybe I’d get more sales. The smart and savvy freelance consultants are the ones who are selling that future of more sales and not just selling a commodity like a website. So I think a lot of us, we’re technically very good at what we do, but we sell the commodity and we wonder, how are we ever going to compete against these $8.00 an hour people off of oDesk? And a lot of people don’t have a really easy way to justify that.
And the example I love giving is this, which is, imagine you’re driving down the road and you need gas. On the left side of the street there’s gas for $10.00 a gallon and on the right side of the street there’s gas for $1.00 a gallon. Which one would you buy? You’re going to go for the cheaper one because gas is a commodity. So when you’re selling design or when you’re selling programming or you’re selling some commodity like that, you’re gonna get stuck in this race to the bottom, right? And that’s why a lot of people struggle to charge more.
And I know in my own agency experience when I learned this and I started to sell solutions rather than deliverables, that’s when we were able to get our team rate up to 10K a week. Each person in my company was billing $10,000 a week. Nowadays when I consult I’m doing more than $20,000 a week because I’m not selling the technicals of what I do, I’m selling – I’m looking at a business, I’m looking at what problems they have and I’m looking at how these problems are affecting their finances and I’m responding to that and finding a way to connect – basically finding a way to build a bridge that goes from where they are today to where they want to be tomorrow.
And that, I think, is one thing I would advise anybody who does any sort of client work. Learn what, why – learn the pain behind the problem. The problem is they need a new website, what is the pain that is at the root of that? And sell the fix to that, don’t just sell the technicals of what you do. And this for me this has been huge. When I started doing this with my own agency, we were selling more clients. It was easier to win work because we weren’t selling the same product as everyone else. On top of that we were able to charge a lot more because I was anchoring our costs against the upside. What would it mean for your business if we could increase your online sales by ten percent?
Well, based on what I know, you’re looking at about this much more money this year, therefore our rate of $10,000 a week is a no-brainer. And that’s what we did and that’s basically what I teach people to do now. And it’s monumental, this mindset shift of going from, “I’m a commodity provider of some service. Yes, I’m technically very good at doing that, but I’m not focused on why people – no one has ever cut a five figure check because they want a website. When you pay the people who work for you, you’re not paying because you care about, really, the deliverables; you care about what those deliverables will enable for your business, right? So it’s the same thing when – I think the savvy consultants and savvy freelancers are the ones who sell that.
John: I love your phrase “building a bridge of where they are today to where they want to be tomorrow.” In Fire Nation, if you can take that phrase, apply it to your business and build the bridge, be the bridge builder of that gap, fill that need, that void, that specific desire, that’s how you’re not just gonna double, but now you’re talking triple, quadruple, be that 10K, 20K bill per week that Brennan’s built himself up to, so I just love that. And Brennan, we’re gonna be extracting some more golden nuggets from you, my friend, in the lightning round. But before we get there, let’s take a minute to thank our sponsors.
Brennan, welcome to the lightening round where you get to share incredible resources and mind blowing answers. Sound like a plan?
Brennan: Let’s do it.
John: What was holding you back from becoming an entrepreneur?
Brennan: The biggest thing for me was comfort. I was in my early 20s and I was doing six figures a year and I was the technology director at an interactive agency and life was good, right? I was newly married and everything was really going great and then my wife got pregnant and she wanted to move up to Virginia, which is where her family was. So I had to leave everything I knew and move, which kind of forced me into freelancing because I didn’t know any businesses up here.
So I just started working with companies I already knew and it was crazy because…young wife, baby on its way, new house, this was, on paper, the worst time ever to go out and leave the safety of the salary gig, but that’s when I did it. And I’m glad I did because at the end of the day, what it’s enabled me is a lifestyle where I’m not working nine to six and then commuting an hour each way to get to the job. Instead I’m able to work from home, go to my daughter’s ballet recitals, drop them off, pick them up from school, it’s the life I’ve wanted. But it was just hard. It’s hard to leave that stability of getting paid every two weeks a decent amount of money.
John: Brennan, you said life was good, and I really picked up on that because, Fire Nation, sometimes the biggest enemy of great is good. We get comfortable. And we get comfortable, we don’t have to push the envelope and get outside of our comfort zone. And Brennan, you’ve gotten a lot of great advice, but what’s the best advice you’ve ever received?
Brennan: I think the best advice I received, when it comes to my business, at least, was when I went down the path of building my own products. And being somebody technical, I’d always kind of dabbled in creating little, quote, unquote, “start-ups” and having them fail and it wasn’t until – I actually took a class, I don’t know if you know her, by Amy Hoy, called 30 x 500.
John: Oh, yeah, I’ve had her on.
Brennan: Okay, this was about four or five years ago. And one thing stood out from that and that was this idea that the easiest way to sell anything is to help somebody make more money or lose less money. And if you can do that, you can convince somebody that you’re product does that. That’s how you sell. Before that I was building all these interesting apps, right? Like I built a Airbnb for homemade meals, thinking that would be awesome, it would scale, huge, everything else. It was dead on arrival. And it wasn’t until I started with my software product to build an app that helped people have better clients and make more money with good [inaudible] software that it just started working.
My products were actually being bought and you can even tell now, Double Your Freelancing Rate is very focused on the outcome, right? It’s very focused on, “Buy this. What would 2X in your income mean for you as a freelancer?” And that’s how I sell it. It’s not about the freelancer’s guide or something ambiguous like that, it’s very specific, even in the title.
John: Brennan, do you have an internet resource, like an Evernote, that you can share with our listeners?
Brennan: The big thing that I’ve loved is Slack, which is a team chat thing, but it’s been great. I’m in probably about ten Slack accounts now. It’s kind of like they’re my masterminds and it’s just been – it’s a great tool. And if you haven’t used it before, think of a chat program that also supports integrating with everything along with file uploads and things like that. I’ve actually started moving all of the things that usually would go to email, like sale notifications or support tickets, to private Slack channels that I’m in and this way I’m able to minimize my email overhead. Some channels will ping my phone, so if it’s a big sale or a support ticket or something, it will notify me. But others are more passive and it’s been pretty nice.
John: Love that. Yeah, I’ve heard nothing but great things, Fire Nation, about Slack. And Brennan, if you could recommend just one book for our listeners, what would it be and why?
Brennan: One of my favorite books that I’ve read recently is Predictable Revenue by Aaron Ross, if you’ve read it or not, but it’s basically – it’s the story of Salesforce and it’s how they sold their accounts and how they were able to build up this predictable pipeline of work. And even though nowadays I don’t really do any high-tech sales, a lot of what the book advocates, follow-up and these different touch points for your customers, is directly applicable, even to lower touch product sales. So it’s been a really good read and highly recommend it.
John: Yeah, I actually listened to the audio version of it and it was phenomenal and, Fire Nation, guess what? I know you love audio, too, so I teamed up with Audible and if you haven’t already, you can get an amazing audio book for free at eofirebook.com. And Brennan, this next question is the last of the lightening round, but it’s a doozy. Imagine you woke up tomorrow morning in a brand new world, identical to Earth, but you knew no one. You still have all the experience and knowledge you currently have. Your food and shelter is taken care of, but all you have is a laptop and $500.00. What would you do in the next seven days?
Brennan: The first thing I would do is I would probably go to Meetup.com and find some sort of networking event that was coming up that week. And I would go there and just spend the day listening to people. Listen to people who own businesses, what business problems do they have, just listen to them talk to me about their problems. And then from there I would just kind of retreat back afterward, reflect on those, and contact these people saying, “Hey, you were telling me about this crazy problem you were having using Excel to run your business. I’ve got some ideas for you. Can I bounce them off of you?”
And again, always focused on solving those problems and pains, right? Same thing applies for consulting and basically from there I would try to land a few clients because, let’s face it, consulting and freelancing is probably, in terms of getting money, a lot of money quickly, it blows just about every other model out of the water, I think. Because you can literally go from nothing to a five or even six figure check pretty quickly.
So I would get my first few clients and then my goal from there would be to come up with some sort of outcome focused retainers that I could convert them to, which would then give me that recurring revenue. And I’d then, skip to work, basically productizing them, so selling them more like products instead of time, and hopefully the rest would be history and I’d have a thriving consulting business.
John: I love how easily you just break it down to how you can actually create something of value for somebody and, Fire Nation, it really can be that easy. Don’t complicate things. And Brennan, let’s end today on fire my friend with you sharing that one parting piece of guidance, best way that we can connect with you, then we’ll say goodbye.
Brennan: If there’s anything, whether you’re selling consulting to clients or selling an eBook to thousands of people, the biggest thing, and I think this is a big take-away from what we discussed today, is just focusing on the problem being solved and the way you’re solving it and what tomorrow would look like, basically for the buyer, for the client, for the customer. And as long as that kind of permeates everything you do, you use that pain in your marketing, you use the upside in the way that you sell, then you’ll have a better business and your customers will get better results.
And if you want to find me, the best way to find me is probably at my website, doubleyourfreelancing.com and I actually have /fire and if you go there I actually have a nine day…or nine lesson pricing course that covers a lot of what we just covered. Just breaks it down into very actionable steps.
John: Awesome. And Brennan, what’s your middle name?
John: Okay, perfect. Fire nation, you’re the average of the five people you spend the most time with and you have been hanging out with BJD and JLD today so keep up the heat and head over to eofire.com. Just say Brennan in the search bar, his [inaudible] page will pop right up with everything that we’ve been talking about, the links to Brennan, to his book recommendation, resources, you name it, it’s there and he has something pretty cool for you Fire Nation. Doubleyourfreelancing.com/fire. Go check it out, make it happen. And Brennan, I want to thank you, brother, for sharing your journey with Fire Nation today. For that, we salute you and we’ll catch you on the flip side.
Brennan: Awesome. Thanks, John.
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