The MapleMoney Show » How to Make Money » Income

Transferring Your Skills Into Income Online, with Michelle Jackson

Presented by EQ Bank

Welcome to The MapleMoney Show, the podcast that helps Canadians improve their personal finances to create lasting financial freedom. I’m your host, Tom Drake, the founder of MapleMoney, where I’ve been writing about all things related to personal finance since 2009.

If you asked a thousand online entrepreneurs how they make money, you’re bound to get a thousand different answers. That’s the premise behind this week’s episode of The MapleMoney Show.

My guest this week is Michelle Jackson, a serial entrepreneur from Colorado who jumped head first into online business when she started her first blog in 2012. Since then, she’s made money as a coach, freelancer, and author, launched a number of digital products, as well as a successful podcast. According to Michelle, almost anyone can make money online by applying the skills they already have.

I’ve often been guilty of saying that blogging is not a great way to make money online. But it all depends on your perspective. The days of the blog as a ‘personal diary’ are long gone. These days, most blogs have become online business platforms. Michelle used this mindset to launch various digital products and services over the past 8 years.

According to Michelle, if you want to make money online, you’ll eventually need to have your own website. You don’t own YouTube, or Facebook. And as helpful as those platforms can be, you have very little control over them. You can get started by using social media, but as soon as you’ve built an audience, try steering them towards your own platform.

Much of our discussion is centered around Michelle’s own experience, which I found very useful. If you listen in, you’ll find out what worked for Michelle and what didn’t, and what she means when she says to “do it ugly”.

This week’s episode was brought to you by EQ Bank. Did you know? You can now transfer money overseas with TransferWise directly from your EQ Bank Savings Plus account. Not only will you benefit from earning 2.00% interest on your savings, but you’ll pay far less for international money transfers. While other banks have a habit of sneaking in markups and extra charges, that’s not something you’ll have to worry about with EQ Bank. Visit EQ Bank to start saving money today.

Episode Summary

  • What drove Michelle to start blogging in 2012
  • If you’re looking to start something online, you need your own platform
  • The story behind Michelle’s first book
  • What Michelle means by the term “Do it ugly”
  • Michelle’s approach to launching products
  • What projects didn’t work for Michelle
  • Michelle’s advice for someone who wants to start something
  • Why Michelle presells all of her products
Read transcript

If you asked 1,000 online entrepreneurs how they make money you’re bound to get 1,000 different answers. That’s the premise behind this week’s episode of The Maple Money Show. My guest this week is Michelle Jackson, a serial entrepreneur from Colorado who jumped headfirst into online business when she started her first blog in 2012. Since then, she’s made money as a coach, freelancer, author, a successful podcast as well as launching a number of digital products. According to Michelle, almost anyone can make money online by applying the skills they already have.

Welcome to the Maple Money Show, the podcast that helps Canadians improve their personal finances to create lasting financial freedom. This week’s episode is brought to you by EQ Bank. Did you know you can now transfer money overseas with TransferWise directly from an EQ Bank Savings Plus account? Not only will you benefit from earning two percent interest on your savings, you’ll pay far less for international money transfers. While other banks have a habit of sneaking in markups and extra charges, that’s not something you have to worry about with EQ Bank. Visit to start saving money today. Now, let’s chat with Michelle…

Tom: Hi Michelle, welcome to the Maple Money Show.

Michelle: Hi, Tom. Thank you so much for having me.

Tom: You kind of dabble in all things online so I wanted to have you on to talk about how you can go from knowing something—you many not feel like an expert in necessarily, but you have this knowledge that’s certainly above normal. How do you take that and actually do something with it? What was your first online endeavor? I assume it was your blog but can you let me know how that all started?

Michelle: In 2012, for some reason, I felt compelled to start a blog. I started it on Bloggers. It was free and kind of rough. My writing was horrible but I loved the process of telling a story. I felt if I could help inspire at least one person with personal finance or let them know that they’re not the only ones struggling with money, then that was valuable. That was a purpose-driven action I could be taking that just took a little bit of my time. I fell in love with blogging. That year I had also started falling in love with all the amazing stories I was reading from other bloggers who were talking about their money situations. Some were really good situations. Others were really bad. Other stories were in the middle where they were still in the process of improving their lives. I discovered, randomly, that there was this event called FINCON that would be in my town literally two weeks later. I randomly found out about this and I geeked out because all of my favorite bloggers were going to be there. I was broke and everything was going horribly but I thought, “Oh, my God, it’s only $100,” and that included food. I’ll never forget that. I thought, “Wow, this is so good. I’m so going.” I walked from my house to the venue because it was walkable and I was actually quiet. This is really weird because for people who know me, I’m its extreme extrovert; very talkative. And a lot of people forget that I was there because I was so quiet because I was fan-girling. It just was such an amazing experience for me. I felt bad for all the people who got sick from altitude sickness. A lot of events hate to return to Denver because of the altitude. They don’t prepare their attendees for it. But anyway, it was just a really amazing experience. I met incredible people. This is something I love, and I still love blogging in 2020. That’s eight years later. I still love doing it.

Tom: People who have listened to this podcast early on have seen me evolve because I literally had episodes warning not to start a blog because it’s not a great way to make money, especially immediately if you’re in need. And I still kind of agree with that but I’ve changed my stance a little because I’m seeing blogging as a gateway to everything else. You start a blog which is probably the easiest thing to start online and then you can spread out from there. And that’s what you did. What came next after the blog? I know you have various things, but I don’t know the timeline.

Michelle: Because I’m insane, I kind of started two blogs at the same time. I started my Square State blog about Colorado around the same time. But honestly, what ended up happening was I just kind of let that project simmer in the background. You really can’t do two things well. You have to focus on one thing and really understand what works, what doesn’t work. From time-to-time I would write an article or whatever on the Square State side. But I felt like I really needed to focus on the personal finance project; Michelle’s Money Hungry because it was much more needed and much more urgent, and it would be harder to grow. And that was the case. But, as I worked on a project, I started to attract different opportunities. I started connecting with different types of people who both helped me and whom I also helped. So it just became an amazing experience. I would say in 2020, if you start a blog, it’s not that you’re starting a blog or starting a content creation business. Even if you just started a podcast, you’re likely to need a website for the podcast. If you start a blog, you’re likely to need a website for the blog because you’re going to need a place that you actually own. I don’t own YouTube. I don’t own Instagram. In my view, anyone who’s looking to start something online and monetize what they know, if they’re wise will absolutely end up with a digital space that they’re paying money for and own which is likely a website. I try to call it a website nowadays versus a blog because I think the function is different now. I’m not… “Dear Diary. Today was really hard because I overspent on lattes and a burrito.” I actually did buy a latte and a burrito today before we got onto this. But that’s not what I’m doing. I am creating an online platform and attracting people to what I’m doing and sharing my skills in multiple ways.

Tom: Yeah, I think the word blog has a negative connotation nowadays anyways. People have been reading my site for a long time. It was the Canadian Finance Blog before it was Maple Money and the word blog drove me crazy. It’s just something I picked quickly because, like you, we just want to get started. As you start to look at it afterwards you see room for improvement. Where did you go next with this? I think you wrote an e-book pretty early on. Is that right?

Michelle: I did write an e-book about Colorado. I wrote it because I got tired of answering questions about my state. I am American. If I had been Canadian, I would have written about my province if I had all of those questions. I just got tired of people asking me all these questions. Even though I wasn’t aggressively working on Square State, I was getting a lot of interest in that project. Since I was tired about answering all those questions, I decided I’d just write this book. And it sold. I wasn’t marketing it. I wasn’t doing anything aggressive. It just lives on the Internet and it sells. That was really cool but it didn’t light me up or I didn’t take notice of it because the amounts were small. But I did notice that it saved me time because I had the book out there.

Tom: I know you also have a course about writing e-books. Speaking about writing about what you know or I should say, marketing what you know, you went from writing the e-book to having a course about writing n e-book so you kind of took that next step along the line.

Michelle: That was weird how that happened because that was a couple of years later. Like most entrepreneurs, we have different interests and we’re multi passionate. But for digital, online entrepreneurs, it’s especially challenging because there’s so many things you can do. If you were to line up 1,000 online entrepreneurs and ask them how they make money, each person would say something different. So in 2018 I realized things were not quite working the way that I wanted them to. Everything was kind of off. So I decided to just experiment and try everything on my list I wanted to try. I had a list of things like services or products that I wanted to sell and I just tried all of them. The reason I did that was just to see what worked and what didn’t work. That year—it was July 2012, I wrote a romance novel. I made $540 the first month and that, I noticed. The reason I noticed that is because my mortgage is $525. That was a mortgage payment (and a latte and a burrito). For me, as an entrepreneur, that was exciting because that is passive income that comes in on the back end. And maybe there’s something to these e-books, both fiction and nonfiction. I decided to also create a course because by that time I had a lot of experience doing things online, in general. I packaged up my what I had learned and sold it. And I sold about $3,000 worth of courses within 6 weeks of that first book being sold. One of the things I learned is I had this whole thing called, Do It Ugly. I think a lot of entrepreneurs and just people in general, want everything to be so pretty. They want the video to be so crisp and their book to be so visually beautiful. There is this expectation of quality that doesn’t match the reality. Until you start doing things, you can’t get the feedback you need to improve the products you’re selling, especially if you’re online. I just launched things and they make money. And when they don’t make money, I figure out what the issues are. So it’s a lot of A-B testing. Now, because of that experience, I’ve made thousands of dollars with both e-books and my course. I’ve served other people and I built in revenue streams that don’t rely on project related work from other people. I should backtrack and say that at the end of 2014, I decided to leave my 9:00 to 5:00 job. I just was feeling like I was going to have a heart attack and die at work. I’m not being funny. I’m being very serious. I was very concerned about my health and wellness and said, “I have to leave. I’m going to die here.” I was having anxiety attacks, eating a lot, gaining a lot of weight. I was really stressed and it wasn’t getting better. It was getting really bad. I just knew I hated working for other people. I really did. I really did. I still do. I hate working for other people. But when you leave a 9:00 to 5:00 job without a set idea of what you can do afterward, a lot of times online entrepreneurs will start as self-employed people. They’ll do a lot of services for other people. I was doing virtual assistant work, freelance writing, that kind of thing. One of the issues I started to have was, even though I loved writing—the craft of writing, at that time, writing for other people was fraught with problems because I couldn’t really say no to clients. I needed the money. I will give you an example of how bad it was. I quit my job and go to Australia and Hawaii for two months. I needed a break to just feel better physically. The stress for my job was so bad that it took a year for me to feel normal, physically. It was really bad. Anyway, I was in Australia for a couple months and before I came back to the United States, I started looking for projects to work on because I don’t want to be broke when I came back. I had a mortgage to pay for so I started looking for things and signed onto, Edit A Book. This is hilarious to me now, but painful. I signed onto, Edit A Book, because I’m just taking any projects, and this book ends up being this incredibly, technical, involved, digital book. Guess how much I said ‘yes’ to? I can’t even think about it now, but I said, “Oh, yeah, I’ll accept $100 for that.” I said yes to probably a $5,000 project for $100. By the time I was done editing that book, I was probably getting paid a penny an hour. And I am so glad that I made that mistake because I learned a couple of things; business people will let you shoot yourself in the foot. But the quality of my work obviously wasn’t that good because I was pissed off towards the end. being right. If you are a businessperson underpaying people, you’re going to get bad quality work (just to let you know). But I had to learn those lessons. Then I started looking at how to make money that was independent of other people so I can say yes or no to projects that serve me well. So I was freelance writing. I made money doing it but it would piss me off because I couldn’t get rid of the bad clients. I had a client who insisted on team meetings but we were contractors and I said, “There’s no ‘I’ in team. I only want to focus on me. Why are we doing this?” It drove me crazy but it drove me to look at how I could monetize what I already knew. The books and the course came from all the years of blogging, all my university work, all my high school stuff. That was years of learning a craft and improving it. There is no coincidence, in my view, that I started doing this. Also, I’m an obsessive reader so it was really an alignment with what I enjoy and value. So when I did the, Make Money With E-Books course… And now I have an academy for it (which is cheaper) it was all in alignment with where my interests are. It’s great now because I stopped freelance writing for about 9 months because I hated it. It sucked. But it sucked because I needed to have the power to say “no” to clients who didn’t serve me well. Now, I am freelance writing again. I added that back in and I love it because I only have good clients. And part of that is because I generate other revenue separate from those kinds of projects. I can say “no” to them.

Tom: Beyond the topic of this show, I find that when people are in any kind of financial issues, it’s hard to make those good decisions. If you’re broke, you’re going to take that $100 job. But once you start to establish some income, some savings, you can step back a bit and make better decisions. In that case you’re finding the right clients and not just taking everything. And also, maybe freelancing to some degree wasn’t for you. You found that courses and everything worked better. A couple of people I’ve seen take blogging into some kind of service, like Steve Stuart, who edits my podcast, was on the show in episode 49. And Ashley Barnett, she went from having a blog as well and is now an editor for blogs. She was on episode 98. Just to have these people that started a blog but then found the next thing… it was just a starting point. The other thing I heard from you there was the idea of failure. Do you have other examples of where you failed? You’re throwing a lot of things at the wall so I assume not everything is going to be a hit.

Michelle: I wouldn’t call this a failure, but just learning what’s a good personality fit… I love being a mentor and I enjoy coaching people. But I got coaching to learn how to become a high-ticketed coach which is a big thing. It just never did light me up as much as affiliate marketing does. I coach people occasionally, but I prefer affiliate marketing. I prefer my courses. I prefer the e-books because I don’t want to really be dealing with people too much. If you’re purchasing a $1,500 coaching package from me, which is actually kind of low for high-ticket coaching, the amount of contact I need to have with you is a lot and I don’t know if I want to be doing that. I had to learn that while I have the skills to be a great coach, it doesn’t light me up and the way that it does other people. So the week after we record this episode, I’m going to a town near the mountains called Salida. I’m going to be working on my books and coursework so I don’t have to engage with other people to do that. I prefer to do activities that are less reliant on dealing with people actively.

Tom: Yeah, that makes sense. You’re finding what works for you and what works for your lifestyle.

Michelle: Yeah. And that’s very much my lifestyle. I would love to be like Michelle Schroeder Gardener and just have affiliate income rolling in. That’s my goal. I just want passive income coming in that is separate from dealing with people actively and doing podcasts. I love, love, love, love podcasting because, as you can tell, I love to talk. It’s a great fit for me. That’s where I focus my energy. I’m starting to reboot Square State so I’m looking at sponsors, self-sponsoring and that kind of thing. It’s 10 times easier for me because I don’t have to manage client expectations in the way you would as a coach. I think just figuring out what’s a good fit energetically as you move forward in your business, is huge.

Tom: Just to get outside of our world of personal finance and blogging and everything, if someone’s listening to this, what can they do? How can they take something they know and maybe don’t even realize is a marketable thing, online and profit from it?

Michelle: I think the first question people need to ask themselves is, what is it that people always tell me I’m good at? If you’re hearing people say, “Oh, my God, your knitting is insane,” knitting is a thing right now because, what else are we going to do? Maybe you are just knitting these incredible, outfits, tunics and random knit shorts (which is a thing that was actually on Shark Tank a couple of shows ago), and people keep asking you how you do it, you could start showing how you knit on Instagram. Build up an audience for that and then let people know, “Hey, I’m thinking about selling your product. Would you buy that from me?” That way you are testing the waters before you create anything. And then based on their feedback you know what to sell. By the way, I presell everything. That way I test stuff out. My academy, which I launched during the pandemic, I thought I’d try out. What else was I going to do at home? And it sold. I didn’t spend on Facebook ads. A lot of people say, “Well, what about Facebook ads?” And I tell them they don’t need to do that. I didn’t spend on Facebook ads. I just kind of put it out there in the world and let people know. And they spent money on it. Was it a huge launch? No, but it was enough money and enough students to validate the idea. And I also had validated the idea based on my course, because the academy is kind of a spin on the course anyway. I learned some things from teaching a course where I thought maybe an academy would be a better use of my time and I could build in a reoccurring, predictable income. So I’m going to be selling both because people learn in different ways. I would never have learned that if I hadn’t experimented first. Another way you could figure out if you should sell a thing is maybe there is a skill that you have that you see everyone selling. I’m not the only person teaching how to sell e-books or to write books. How many people are out there doing that? There are tons of people. If there are tons of people selling a process that you’re interested in, then it means there’s room for you to do it too. Just in the U.S. and Canada alone, if you’re an English-speaking entrepreneur, there’s 400 million people that you can serve, the entire North American continent. And if you speak Spanish, add the other 56 million. My point is there’s plenty of people to serve. You need a much smaller percentage of people that you think in order to make a difference to your bottom line and to other people. It’s taken a very small number of clients, to be honest, to change my life. I don’t need a ton of people because like I said before, my mortgage is $525. I don’t need a ton of people to purchase my products. I want a ton of people to purchase them but it doesn’t take a lot to change your life. Think about it this way; if I make $500 a month with my e-books, that’s $6,000 in a year. When the border’s open, (maybe not for Americans) after the virus hopefully ends, that’s a she-she European vacation or a semester of tuition here in the U.S. Or it is a used car– $6,000. Or that is a payment on debt. That is a significant amount of money.

Tom: One thing you mentioned was that you were able to test out your next product. And I think that goes back to the benefit of having a website, having that base. I know there will be people listening that are thinking, “What do I do when I don’t have anything? I’m starting from scratch.” You mentioned Instagram in the case of the knitting example. One thing I’ve seen a lot during this whole Corona virus, we’ve got people here locally that have teaching exercise classes. My kids are in piano and guitar classes online. And this is all new to all these people. They were kind of forced into it but I think this whole “new normal” idea might see larger companies doing more of this. What should they do? Do they just rely on that “in-person” base and try to spread from there?

Michelle: Are you asking what brick and mortar businesses do during a time like this?

Tom: Yes, but even if it’s just someone from home—if you are just a person who knows about something and is looking to do something. Obviously, the brick and mortars can benefit from their current people. But if you’re that mom that loves exercising and you want to do something there, too. Maybe you can speak to both?

Michelle: I would say now is the time. In the United States there are a lot of people who, especially when the pandemic first started, were saying you shouldn’t be selling anything. And that it’s a bad idea because people are losing their jobs. If you are not selling right now, you’re insane. There are families with little people who are freaking out right now because they don’t want to send their kids to camp but they need to keep their kids entertained so they can actually work. They need to educate. If you’re an educator, parents need help with educating their kids. If you are a wonderful mathematician and you actually like kids, then start an online tutoring business. If you are a person who is all about organization skills, moms and dads at home are saying their homes are a mess and everything is disorganized so you could do one-time webinar. Just record it and then people could purchase it. They could just buy it and watch you organize or whatever and learn those skills. It is 2020 and it is crazy not to be leveraging the internet to sell what you already know. I am a Gen-Xer so I don’t want to hear I don’t want to hear, “I’m such-and-such age and it’s really scary,” because that’s crap. Get on YouTube and learn how to do it. I learned a lot of this by literally Googling; how do I do this? And watching YouTube videos to show me how to do my blog and asking questions from other people. You are 100 percent capable of learning how to do this and it’s not as hard as you think. A lot of the skills you’ve already developed at your job whether you work at Starbucks as a barista, which are a lot of soft-skills and people-skills. Or if you work for a major company, it could be skills on organizing projects or project development and you can apply those online. So if you are not selling something or sharing a skill or your wisdom online in 2020, and you’re sitting there and thinking, “I need more money to pay off debt. I need more money to save. I need more money for my dream vacation. I need more money just for my peace of mind. I need more money for the wedding that I postponed this year…” you need to get started online and you need to get over yourself.

Tom: Yeah, it’s the idea that you don’t have to go all-in, full-time with this, literally, if you have that debt you want to pay off. Any kind of income is good. The numbers don’t have to be huge. If you can make that $500 it goes a long way and gives you that bit of freedom and the ability to step back and make better decisions. Can you let people know where they can find you online?

Michelle: You can find me at You can find on Instagram under Michelle’s Money hungry. And on Twitter @michlovesmoney. I also have a tool kit in case you would like to start your podcast, blog or whatever you have. It’s called, Do It Ugly. Again, I believe you just have to get it out there. It does not have to be pretty, perfect, doesn’t get paid. So just go to and grab that resource. Or you can text 66866 Money Hungry and get the tool kit there.

Tom: Great. Thanks for being on the show.

Michelle: Thank you for having me.

Thanks Michelle, for showing us so many ways to get started with an online business. You find the show notes for this episode at Are you new to the Maple Money Show? If so, I want to thank you for listening. In case you weren’t aware, you can watch videos for many of our top episodes on our YouTube channel. If interested, head over to and hit the subscribe button. I look forward to seeing back next week when we have Andrew Kerr join us to discuss all things house hacking.

Until you start doing things, you can’t get the feedback that you need to improve the products that you’re selling, especially if you’re I just launch things, and they make money. And when they don’t make money, I figure out what the issues are. - Michelle Jackson Click to Tweet