The MapleMoney Show » How to Make Money » Career

Stuck in a Rut? Here’s How to Start Making Extra Money Today, with Philip Taylor

Presented by Borrowell

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

My guest this week is Philip Taylor, of PT Money. From college side hustler to full-time entrepreneur, Philip has been writing about legit ways to make more money for over a decade.

Starting a business while balancing the demands of a 9-5 career can be challenging. In this episode, Philip explains a number of ways you can make your business or side hustle fit your lifestyle.

Our conversation is wide-ranging, as we address the concepts of trading time for money, why freelancing can be the perfect side hustle for bloggers, and when and why downsizing your career just might be the best decision.

Philip also shares his secret to making real money through freelance marketplaces like Fiverr. It’s an episode you don’t want to miss.

This episode is made possible by our sponsors at Borrowell. Borrowell is a Canadian company that can help you check your credit score within minutes. A better credit score makes it easier to obtain a mortgage, a personal loan, even get better rates on insurance. To check your credit score with Borrowell, head over to their website today!

Episode Summary

  • Why finding additional income from your career can be limiting.
  • How to find a side hustle that fits your current lifestyle.
  • When and why downsizing your career may be the best decision.
  • When daycare can be useful for the entrepreneur with kids.
  • How your spouse can support your side hustle journey.
  • Five ways to find the ideal side hustle.
  • Never go into debt to fund your side hustle.
  • Why you should always be thinking scale.
Read transcript

Welcome to the Maple Money Show, the podcast that helps Canadians improve their personal finances to create lasting financial freedom.

Do you feel like you’re stuck in your job barely getting raises that rarely keep up with inflation? Thankfully, there are infinite ways to make money especially with the growth of the internet and the peer-to-peer sharing economy. For this show I wanted to bring on my good friend, Philip Taylor, from PT Money. Phil had various side-gigs back in college has been writing about legit ways to make extra money for over a decade.

Our sponsor, Borrowell, is a Canadian company that can give you your credit score for free within minutes. Having a good credit score can help you get better rates on your mortgage, insurance or personal loan. Those three digits help you save money. You can find out more at

Now, let’s get to PT…

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

Philip: Hi Tom, thanks for having me. And congrats on the new show. I’m honored to be a guest.

Tom: I wanted to talk to you today about ways to make money. The reason I came up with this topic with you is, as far back as I can remember, I think it’s the first thing I remember you for. When I met you online in 2009, 2010, this was something you were writing about. It changed my mind-set because I was totally focused on just how to save money and this was a different angle I wasn’t even considering.

Philip: Yeah, making extra money has become a passion (for sure) for the past 10 years of my life. Like most people, I was a dude thinking I’ll graduate from college, get a job and just kind of go on with my life. But, I found myself dissatisfied with that job and that career so I started looking for a different ways to do something different. I didn’t know what that would be. I dabbled around in a few things. I eventually found my way to doing some blogging and other things. My side-hustles lead to some real businesses for me that took over my life. I’ve kept some side-hustles as well—we can get into some of those later. But yeah, it’s been a real fun journey of discovering the other side of the balance sheet, or the income statement, rather of making the most of the income side of things. You’re right in that expenses after awhile kind of get boring because there’s only so much of them you can cut. What I’ve found in my life is that I was hard-core—slash expenses, get it way down and try to live really lean. Then I wondered, what do I do now? If I was spending  $3,000 I could only drop that down to maybe $2,000 or $1,000 and live really lean. But now? What’s next? Obviously, we’ve got to look at the flip side of the coin. Let’s try to work on some more income. It’s been a fun journey to play around with the topic, write about it then run a couple businesses myself that have become successful has really changed my life. I’d encourage everyone out there listening, if you’ve started working on your finances and you’ve played around with the expense side of things, you have to start flipping the switch and think about ways you can bring in extra money. And I’m excited to share some of those ideas with you and your listeners today.

Tom: It seems like a simple question but why do you think someone should be making more money? I still have a regular day job and I’ve talked to a lot of people and their mind-set is, the only way they’re going to get more money is to get a raise. There is no, “Oh, I could go and deliver pizza,” or something like that. In your opinion, why should people be looking at these ways to get extra income?

Philip: Well, we’ve already hit on one which is to improve your financial life. You’ve got expenses you can reduce and income you can increase so one reason is because you can do something about it. There’s an exponential opportunity there. Your income is not limited, necessarily. And through your job is a good approach as well. People should pursue that if they have a career. They should look for more ways to make money through that career, put themselves into that and seek raises, change jobs and try to get more income. That’s cool, but again, that’s a slower path. There’s less wide-open opportunity and less under your control. When you start talking about ways to make extra money or start a business on the side, side-hustling, it’s often times fully under your control. Given that, that independence and autonomy with the thing, if you get in there and start having some fun with it, who knows what can happen. But extra income in your life can do a lot of things for you. It can help you pay off debt faster if you’ve got a debt-reduction goal. Maybe you’ve got some student loans—even paying down your mortgage faster. It can help you advance really quickly with your financial life. That’s what it did for me and my wife early on. Another couple of reasons why is, life changes. As you have kids or advance in your career you may be saying to yourself, “I kind of want to be home with my kids,” or you just want to give the entrepreneur thing a try. Just straight jumping out of a career and into entrepreneurship is a recipe for disaster, in my opinion. I like the side hustle ideas because they allow you to transition into that space. It’s a way to test the waters. Other reasons include starting some investing. If you’ve found yourself not able to invest as much for the future with your current paycheck, then by all means, go out there and get a second source of income. It’s going to create some income diversity for you and a little more security in your life when you’ve got multiple sources of income. That’s ideal as you age. As the old wise man would say, you should be able to dip your hand in different money jars out there and have a lot of different sources of income coming to you. To me, there are more than enough reasons out there for people to at least test it out. When I tested it out it was fun. And if it is fun, then it’s something you want to do. And, if it’s something you want to do then it’s like, “Oh, this could be something that’s really big for me in my life.” It’s just like anything in life… you want to discover new things. I think discovering new paths for income is something you should keep an open mind to.

Tom: Another thing I hear a lot (especially with the water-cooler talk at my job) is that nobody has the time. They say they already have a job so they can’t do too much in the day, obviously, and they always want to relax and watch TV and stuff in the evening. How do you think they can find that time? I know on my side—I was just admitting to this last episode, I was losing too much sleep so I was probably going too far overboard. Are there other ways where people can still sleep, still have a job and find some time?

Philip: Yeah. I have a few ideas on this topic as well. The first one I would say is look for money-making ideas that are on the way, or while you’re away. This is the sharing economy. I drive downtown every day so I can potentially become a  Lift driver. I just turn my device on as I’m heading into downtown every day. The same thing on the way home. Or whenever I go to the airport—whatever it is. You start dabbling in these ideas, this sharing economy out there that really doesn’t take you out of your normal everyday life. You’ve got to be careful with this because it could creep into a bigger experience for you. That might be cool too but just look for ways that sort of fit in with whatever you’re already doing. You may have a bunch of extra stuff around the house that you could get rid of and sell on one of those online websites and aggregators. Look for any idea out there that’s on the way to something or while you’re away. If you go on vacation or go off for business several times during the year, you might consider renting your house out through an Air B&B service. Just put yourself in that mind-set. Think about what your normal day is like and how you can insert a different money-making idea into that routine. Secondly, you already mentioned it… the crushing hours. We spend about eight hours a day working at our normal jobs, then we spend about eight hours sleeping so what do we do with that other eight hours? You could take in the family, take in a little leisure activity, get some extra sleep in or put some extra work in maybe. You’ll probably end up with about two hours still left of the other eight hours so I would start there. What worked for me was using my nights and weekends. Even extra time at work on my lunch break or during breaks. If you really want it bad enough, you’ll find the time. Thirdly—and this may be a little controversial but consider downsizing your career. For me, I went to a job that I knew had less responsibility. I went from a management position down to more of an analyst position in my corporate career and that allowed me extra time. That was sort of controversial at the time and the pay was still about the same but I knew I was going to step back in my career direction. I knew I just didn’t want to be in that career. So if that’s you out there, if you feel as though you’re heading up the ladder but it might not be the right ladder, maybe you should think about what you could do to still hedge yourself to stay in a career but allow for more time to explore some other ideas.

Tom: I had a similar thing. I didn’t necessarily have to step back but I hit the point a few times where I’ve gone out of my way to make sure I’m not advancing in my career. I’ve had no interest being in finance, getting designation, being management or director or anything like that because I’m at a place where my day is full. Between kids, my online business and the day job, the idea of putting more time into my career just doesn’t make sense when there are other things I could be doing with that time that are, hopefully, more productive.

Philip: I love it, yep. I’ve got two more for you.

Tom: Yeah?

Philip: One is daycare. Weigh the cost of having someone else watch your kids for a little bit against the potential income you could make (even if it’s just for a couple hours a day). Even if you have to barter it. Say you’re starting a business that services other people in some way. Consider bartering somehow with the service you’re going to be providing them with watching your kids for a couple of hours. Always put that on the table if you’ve got kids. Lastly, if you’ve got a spouse, think about it from the teammate prospective. You’ve got someone else in your life that’s sharing this income with you. Maybe seek out help from them to make this possible—to make this happen. I think of Steve Chou and his wife. They started their online store over at—oh, what’s Steve’s website—

Tom: My Wife Quit Her Job.

Philip: That’s it, My Wife Quit Her Job. He tells a story of how he and his wife started while he still had a full-time job. I think that’s a good route as well, to enlist your spouse to be that person that helps. Not only does that free up time for you, it becomes part of the business as well. Maybe they can bring their assets and knowledge into it as well. I think there are lots of ways you can think about it. Again, if you want to do this bad enough, you’ll eventually find some ways to fit it into your life.

Tom: I know Gary Vaynerchuk had a famous quote. It’s a little dated now but he said, “Stop watching f’ing Lost!” It’s just this idea that (more now than ever) people can actually binge watch four of five hours of Netflix in a night but can’t seem to find any time to work on something else on the side. It’s priorities. If someone wants to make this work, they definitely can.

Philip: Yeah, and there are seasons in life. You go through this for a couple years until you’ve got the thing off the ground and then it becomes your full-time thing. Then you can have your lost time back. But, dedicate some time when you’re young and you’ve got energy to do something like this.

Tom: At the beginning, you mentioned that you had some side-hustles during college. What were you doing then?

Philip: I tried a bunch of different things. I was all over the place. I waited tables which I think is a great side-hustle for nights and weekends because that’s when most of the cash is made if you’re a server. I also think it’s a good job to have to make you a better human because you’re in a position to serve someone and you have so much more empathy for a person in that position for the rest of your life. I made some good cash. I also parked cars. I worked for a car parking service outside of parties or fancy restaurants. That was another quick-money thing for after work. I made some pretty good cash in tips.

Tom: I was just going to say, with most of those jobs do you actually make more in tips than pay?

Philip: Absolutely, yes. Tips are where it was at and I would try to max out those as much as possible. Whatever I could do to please the customer and make it a better experience for them, be faster, be better, be nicer—whatever it was to maximize those tips. Those are sort of trading times for money, those types of side-hustles. I think they’re good for a season. They taught me some lessons but it was hard to scale them because, essentially, they were just side-hustle jobs so I moved onto different types of opportunities. The next one was when I learned how to blog myself. Then I started making websites for other people. I found local businesses that were in need. This was something I could scale pretty quickly. Anyone who asked me how I made my website or how I did blogging, I would offer the service to them. I could hook them up, set them up with their own site and do it really quickly. I think I was even getting the hosting company commission for the affiliate as well off of it so it was pretty cool. It was a double-dipper there but, that was a really good one. Then, as I continued with my blogging efforts—and the blog, in some ways, was a side-hustle but freelancing was another one I really enjoyed because it taught me to be a better writer. It got me out there, taught me about subjects on personal finance which I’m passionate about. It brought in some nice extra income on the side. Freelancing is something I think a lot of people can do as a side-hustle if they have a kid at home. They’ll really be able to ramp up their income pretty quickly.

Tom: Yeah, it’s not a guaranteed payment but at least they know the payment they’re getting with a particular client, unlike blogging where you can easily go six months and not make anything.

Philip: Yes, it’s a long-game for sure and that’s why I think it pairs well. Freelancing pairs really well with blogging because you can do both simultaneously. One is the instant payment while the other is the longer play. A lot of times people that work on the internet space take that approach regardless of what business they’re doing. They’ll have a freelance element to what they’re doing while they’re working on this long-term play. And that’s smart because you want to eventually work towards something that’s scalable. That’s the best kind of side-hustle to run. It can serve a lot of people rapidly.

Tom: So, things like blogging and freelancing have become possible because of this whole online thing. I know there’s a ton of different online service that have made things possible that we didn’t have before. You mentioned, Lift, before. I think they’re in Toronto right now. Uber’s around a lot more in Canada. What has the internet opened up to us with different services and ideas? Almost anyone can start a side-gig in the next five minutes.

Philip: Sure. I’ve got a good article on this called, Fifty-two Ways to Make Extra Money, so I’d encourage folks to check that out but I’ll definitely share a few of those ideas here. One that comes to mind is a site called, Fiver. Many people have heard of Fiver at this point. The trick to Fiver is not doing the five-dollar gigs, it’s selling the up-sells. It’s kind of like freelancing in that you’re doing the five dollar thing but you can also offer these up-sells for $30, $40 or $100. I did a podcast interview with someone who told me that’s the secret sauce; make sure your up-sells are of high quality and you’re charging a good margin. The other one I like is a new one called, VIP Kid which is for any teachers out there or people who think they would just enjoy teaching. VIP Kid allows you to teach English to students in Asia. It’s an online portal that allows you to do that. Folks are reporting that they’re making some pretty good money through that program.

Tom: Do you need any kind of teaching experience on that or a certain English level?

Philip: Nope, I think you just pass some initial tests with them. And it’s sort of an open marketplace so I’d encourage anyone who has a knack for teaching and speaks English to check it out. I looked it up and it looks like Canadians are doing it and there is a big advantage to Canadians doing for tax reasons (I believe). I can’t get all into it but apparently you can keep a lot of the money as a result by the way they’ve structured it.

Tom: Interesting.

Philip: Yeah, that’s VIP Kid. Another one we talked about briefly before the show was called, Rover. It’s an online portal to help you take care of folks’ pets. So, if you like dogs, cats and you want to be a house-sitter for those pets. This is another one of those “on-the-way” jobs. If you find yourself walking your dog all the time and taking care of your dog at your house, maybe Rover is for you. Maybe you can hook it up and find some other people to help out and make some money taking care of their dogs too. I think I have a few others on the list. None are coming to mind right now, Tom, but if you have any that could refresh my memory… Those are just a couple of the new ones, fresh ones out there.

Tom: There are a couple of Canadian apps I wanted to sneak in here because I know you won’t know them. There are a couple I like that are specifically Canadian. One is, Drop. Drop is an app where, when they connect to it they can basically see their spending. They’ve connected their cards and stuff and they give you additional rewards. We’ve already got our credit card rewards. We’ve got our Air Miles here in Canada and Aeroplan, Drop just adds another layer of rewards on. Basically, there is no extra effort. You’re getting all this free stuff just by connecting to the app. Another one I wanted to mention on a different angle is, Lending Loop. It’s sort of a peer lender. It’s probably the only one in Canada that lends to businesses. Not person-to-person but you can lend to businesses. It’s an interesting way to make extra money that isn’t a traditional thing (like what we’ve been talking about). It’s not a gig but it’s an interesting way to make money here in Canada.

Philip: I like those. That kind of jogs my memory. In the US there are things like, Swagbucks. There are survey companies you can tap into. And some of these are really legit and it’s something you can do from your computer. In some ways it’s kind of passive as well. Some of these will literally pay you for surfing the internet. I think once you set your mind to finding some of these things and seeing which ones are passive, you can set yourself in motion. They’ll start coming to you. As technology advances, more and more these ideas are coming down to us every day so it’s pretty cool.

Tom: Yeah, I like the survey ones. I recommend a few of the legit surveys. They get a bad name because there’s a lot of junk out there. But things like Swagbuck or Opinion Outpost are ones available here in Canada as well. Even if you want to binge your Netflix, you can still be responding to a survey. They don’t come all the time but when they do come, you might as well fill them out. They want to know your opinion and helps feed advertising dollars and everything like that.

Philip: Also, if you know you’re doing this because you want to pay off your debt, for instance, you can get by doing some surveys or doing some boring internet work for awhile knowing that you’re advancing your financial life. I’ve got some tips (in general) for folks if they want to get into doing something on the side and I’d love to share them with you.

Tom: Yes, for sure. To add to that, how do people decide what they’re going to do because you’ve got a huge list of items on your site and I’ve got another huge list. Combined we’ve got at least 100 different things people can do. So yeah, how do they get started and how do they choose what’s right for them?

Philip:  A couple of things come to mind here. I think if you’re young, oftentimes you can trade time a lot more easily so it’s okay to come up with ideas that trade your time. As you get older you’ve got to get a little more slick about this and hopefully build something that creates a little more passive income for you and be a little more smarter about it. The way I think about it is, I’ve got five things listed here. The first is, look for ideas that are proven in the marketplace. Don’t think you have to create the next Lift or next Facebook. Just straight-up copy-cat people. People are talking all the time about what they’re doing online to make money. I’ve got 25 or 30 podcasts on how people are making extra money for themselves and you’ve got all kinds of articles on this topic. Go out there and see what’s actually working for people. People are sharing this online. Find the thing that resonates with you where you can say, “Wow, I can really do that because I’ve got that amount of time, I don’t have to invest all that money and I really like that aspect of it.” If you find yourself resonating with some of these ideas then go and explore them. The ones that make sense to you, go after them. Don’t be afraid to copy-cat. Next, I would just say it should be fun for you. If you’re really going to put enough energy into this thing to eventually make some money and possible eventually scale, make sure you’re doing something that’s fun. Don’t trade the corporate ladder you’re dissatisfied going up for another ladder you’re dissatisfied going up. Go to another ladder you’ll enjoy climbing up. Third, I would say, absolutely no debt. Don’t pay money to be part of a program to make money. Don’t go into debt to do any of this. You’re going to hear all the time, “I’m a small business owner and I need to have a credit card immediately to be able to do this or that.” No, no, no, no! Bootstrap this thing. Don’t spend money until you’re making money. Have that mind-set going in. That’s helped me and that will help you going forward. To that point, use this as an opportunity to fix your finances. As you’re coming up with this idea, and as you start developing it, think about, “If this is going to be my thing one day then I’m going to spend, not only this time learning about this new idea and exploiting it and making some money, but I’m also going to spend some time fixing my financial life so that when I am ready to make the full-time leap as an entrepreneur, then my finances are in good enough shape that it will totally be easy to do that.” So, you want no debt in your life, emergency savings all built up. You teach people all the time how to do this stuff but make sure the making money side is helping that finance side so when it comes time to make this side-hustle a bigger thing, you’ll be ready. Lastly, I would suggest you focus on things that do scale. I challenge you to come up with an idea that won’t scale. I think most of them will. Think about the business and how you could… this kind of goes along with the fun part of it. To me, fun is a business that you can grow. That’s really fun once you get into it. If a business is struggling to grow or you’re having trouble seeing how this could serve a lot people and make you a lot more money eventually, then maybe it’s the wrong one. Or maybe you’re thinking about it differently. For instance, I like to use the dry cleaner analogy—the dry cleaner service as an example. I own the store on the corner and everyone in the surrounding neighbourhood comes there, drops their clothes off in the morning. I dry clean their stuff and at the end of the day they pick it up and they pay me. That’s a limited type of business. It’s probably a good cash-cow but it’s only going to make around $100,000 a year. It’s never going to make more than that unless you go and buy other dry cleaning businesses and start a franchise around it. That’s one way to scale it. But maybe even a faster way to scale it would be to master the idea of how to make an awesome dry cleaning business and then teach people online how to make their own dry cleaning business. To me, there is always a way to scale something much more rapidly. Maybe even through creating the dry cleaning business you come up with some awesome technology that can serve all the dry cleaning businesses across the United States—put that kind of thinking cap on whenever it comes to these businesses or side-hustle ideas. How can you take them and serve the whole world with these ideas? I think that’s really exciting. As you can see, I’m getting kind of antsy about this but that’s where the fun comes in. As you think about it, this kind of thing can really change your life. It has for me so I’d encourage people to get in. Get in right now or as soon as possible.

Tom: For sure, this has been awesome. Before we go, can you let everyone know what you’ve been up to and where they can find you?

Philip: My main personal finance site is called, I encourage you to come and check out all the cool money-making ideas and articles we have over there. Then, of course, I run a conference for personal finance bloggers called, FINCON. If you’re in the business, I’d love for you to come and check it out. We also have a “community” pass this year so if you’re just a personal finance geek and don’t necessarily have a blog but want to come check it out, we’d love to have you. Take that community pass. That’s at;

Tom: And it’s in Orlando this year so it’s a great reason to head down.

Philip: That’s right. Come on down.

Tom: Thanks for being on the show.

Philip: Absolutely, Tom. Thanks for having me.

Thanks again to Philip Taylor for sharing his thoughts on making extra money. You can find show notes to this episode at We’re already up to episode six in the Maple Money Show. If you haven’t heard all of them, I encourage you to go back into your favorite app or to so you’re not missing out and you can catch other great guests like Jessica Moorhouse and Pat Flynn. After you’re caught up, leave a review and let me know what you think.

'Freelancing pairs really well with blogging because you can do both simultaneously. One’s the instant payment and one's the longer play' - Philip Taylor, on the relationship between freelancing and blogging. Click to Tweet