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How to Start an eBay Flipping Side Hustle, with Jason Butler

Presented by Wealthsimple

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’re like anything like me, you’ve spent plenty of money shopping online over the years. But have you ever considered making money on sites like eBay or Amazon? That’s what my guest this week does, and he’s here to tell us more about a very unique side hustle.

Jason Butler is the owner of My Money Chronicles, a website where he discusses personal finance, side hustles, travel, and more. Jason is from Atlanta, Georgia. He graduated from Savannah State University with his BA in Marketing. Jason has been featured in Forbes, Discover, and Investopedia.

Jason explains how he got his start reselling items on eBay, and why he prefers it over other side hustles he’s tried in the past. Jason sources items a variety of ways, but at the moment, he says thrift stores are his favourite place to find products to sell. He even shares examples of some of his top finds.

Jason’s advice to anyone interested in reselling on eBay is to just get started. There’s no cost to create an eBay account, and you get 50 free listings per month. From there, start with what you know. Jason is a big sports fan, so he started with jerseys, running shoes, and bobbleheads. To get the rest of Jason’s tips, you’ll need to listen in to this week’s episode of The MapleMoney Show.

Our sponsor, Wealthsimple, believes that financial independence should be available to anyone. That’s why they have no account minimums, meaning that you can get started investing for as little as one dollar. Don’t delay any longer, invest online by visiting Wealthsimple today.

Episode Summary

  • What got Jason into reselling items on eBay
  • How shipping works with a reselling business
  • Jason explains his process for finding products to sell
  • Best places to find items to sell
  • Why Jason doesn’t sell on Amazon
  • Other side hustles Jason has tried
  • Why side hustles make sense in the COVID-19 era
  • Jason’s advice to those who want to get started
Read transcript

If you’re like me, you’ve spent plenty of money shopping online over the years on sites like eBay and Amazon. But have you ever considered making money by reselling products online? That’s what this week’s guest does and he’s here to tell us more about a very unique side hustle. Jason Butler is the owner of My Money Chronicle’s website where he discusses personal finance, side hustles, travel and more. Jason graduated with a BA in marketing and has been featured in Forbes, Discover and Investopedia. On the show, Jason explains how he got his start reselling items on eBay and why he prefers it over other side hustles he’s tried in the past.

Welcome to the Maple Money Show, the podcast that helps Canadians improve their personal finances to create lasting financial freedom. Our sponsor, Wealthsimple, believes that financial independence should be available to anyone. That’s why there are no account minimums meaning you can get started investing for as little as one dollar. Don’t delay any longer. Invest online by visiting today. Now, let’s chat with Jason…

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

Jason: Hey, Tom. Thanks for having me.

Tom: You’ve got a really interesting side hustle I really like, flipping items on eBay. Going back to the beginning, what started this? What was your financial situation like? What made you tweak to this idea?

Jason: Well, before I got serious about it, I’ve pretty much been dabbling in eBay for the last 10 years. In 2015, I decided to get serious about my finances and start paying off my debt. And I was looking for multiple side hustles to help me with debt. I realized I could sell things on eBay. I’m a big sports fan and at the time I had a couple of jerseys I didn’t need any more and some old tennis shoes. I wanted to see if those items would sell. I actually put my old Jordan tennis shoes online and I sold them for $45. So I figured this was a side hustle I could try. I started to go to thrift stores maybe once or twice a month. I went to a Salvation Army and found a jersey for $3, listed it for $45 and it sold within 72 hours. I was hooked because that was a $42 profit. You can’t beat that. Ever since then, I’ve been getting more and more serious with selling things on eBay. And instead of going to the stores once a month, I literally go twice a week now.

Tom: That sounds awesome that you’re selling a jersey with that much of a markup. How does this work out, though, with the costs of things? I assume there’s a cost to list things on eBay. There is a cost for shipping. Does the buyer pay the shipping?

Jason: I have an eBay store so I get up to 350 items listed for free. The thing is my store does cost $21 per month. But at the end of the day, it is worth it because I’m making a lot more to $21 a month online with eBay. When it comes to shipping, you can do multiple options. You can either pay for shipping yourself or you can let your buyer pay for shipping. For the majority of my items, the buyer pays. I just include that price inside the item I’m selling because I’ve been doing calculated shipping for the last 5 months. I have a scale and a printer so I do everything out of my house. Now, back in the day I used to estimate or put a shipping price on, but that shipping price might be too high or too low so I ended up losing money doing that. For now, I do calculated shipping and the buyer pays.

Tom: It seems also on eBay that sometimes people may be using shipping as a way to profit. For example, there may be something that’s on there for $2 or $5 but the shipping is $10. It’s like they flipped it compared to all the other listings.

Tom: When you see listings like that, 9 times out of 10, it’s some kind of money laundering scheme. Seriously, eBay has a good way of checking listings but the thing is, there are millions of items listed per day. They can’t check everything. There are some smart criminals out there that do some kind of money laundering. I’ve seen it with lots of different items like VHS tapes, Beanie Babies. It’s like you said, you can see a jersey selling for $1 but the shipping is $80. That is some kind of laundering scheme or they’re just trying to do something that’s not 100 percent legal.

Tom: Yeah. I didn’t even think of that. I was thinking at the very least, they were just trying to make it look like the product is cheaper where if someone is not looking at the shipping price and just focused on the listing price.

Jason: And what is crazy is that eBay still gets a percentage of the shipping but is nowhere near as much as the sale of the item. So that’s another reason why they do that too.

Tom: When you’re going into the thrift stores, how do you do all that? From the moment you go into the store, how do you know if you buy something, that’s it’s going to sell for more. How do you know you’re not getting a bad deal?

Jason: I’ll give you my rundown. As soon as I go to the thrift store, I literally go straight to the shoes first. I check out the shoe section and then from there I look in the clothes being the DVD and video game section, then toys. And the reason I do that is because there isn’t much in shoes so it’s the easiest place for me to look in. And I’m always with my phone. eBay has an app that you can download on any Droid or iPhone. Basically, it’s free. You can type in any item you’re looking for. Let’s just say I’m going into the thrift store to look for some new Jordan’s. I type in the name of the Jordan’s and the and there’s a section on there where I can click “sold” that way I see if the item sold for a high amount or a low amount. I do that with a lot of the items in the thrift stores. But the good thing is, after you sell for a while, you’re comfortable. You know what sells and what doesn’t sell. When it comes to Jordan’s, I don’t really research that much anymore. And for jersey’s, definitely not because I’m a huge sports fan. I love baseball, basketball and football. I know the good players and all the players that suck. If I see a jersey of somebody that’s good, I’m going to buy it without doing research if it’s a good price. What I do now though is try and get out of my comfort zone and sell different types of items. I’ve been selling different types of board games and other different items as well, like coffee mugs, because at one point I was only selling Starbucks coffee mugs. But there are all types of brands out there. I just pull out my phone and do the research when I’m in the store.

Tom: I know you’re spreading out to different items but you still have a niche with the sports so that you actually know the items. On your site, didn’t you sell women’s pads or something like that?

(Lots of laughter from both Tom and Jason).

Jason: Yeah, it’s funny you brought that item up. This was probably about 6 months to a year ago. I’ found a box of 1984 or 1985 vintage, maxi pads for $3.26 and my gut instinct told me to just grab them. I did my research and saw they were selling between $50 and $200 so I figured, what the heck and just grabbed them. I ended up selling them in a few months for about $50. That was a great flip for something that was 30 some years old.

Tom: Wow. So it really is about the research then, I assume, even for items you obviously know nothing about. I was thinking you had to go in as an expert and truly know that item.

Jason: No. When I first started getting serious, I was testing so many items out so a lot of stuff sat for a long time. At one point, I had items from 2017 still in my store and it was 2019. Right now, at this point, I only have three items that from 2017. But if we go back about a year ago, there were probably 50 items. I started lowering the price just to get that stuff out of here. Most items usually flip within three months. items.

Tom: Fifty items doesn’t sound too bad. I kind of had this picture in my head of you having half a garage full of inventory. Does it ever get too bad? Maybe even with people you’ve heard of?

Jason: It doesn’t get too bad. At one point I actually had 250 items in the store. But because of COVID, people have been scared to go out so they’ve been buying a lot online. From March, I was at 250, which was my highest ever. Now I’m at 173 which is crazy. This is a good problem to have because stuff is selling and I’m making money, but at the same time, how eBay works is that the more you list, the more you sell (in a lot of cases). So I’ve been trying to get the items in my store back up. I haven’t been able to get there yet because stuff is still selling. But I’ll get there.

Tom: You said you got stuff from thrift stores. Have you tried other ways? Even on eBay, do people sometimes sell it for a bad price and you can kind of flip it there? And I’m even thinking about garage sales and things like that.

Jason: Great question. I’ve been to a couple of garage sales. I went to one in July. I literally got six board games for $6 total. And these board games were selling for anywhere online from between $25 and $100. I’ve sold two of them already. I’ve made something like 11 or 12 times what I put in so that’s great. When it comes to more sourcing, I also look online. I check eBay out. You will find sellers that don’t know what they’re doing from time-to-time. People are just trying to get rid of stuff. Whether it’s eBay, McCarry, Poshmark—they have items listed for a cheap price. So I go in and buy then resell it myself. I recently got a coupon for $25 off for some items. A lady had 6 bobbleheads listed it for $19.99 so I bought them. The only thing was, I had to pay for shipping and it was something like $13. But I’ll easily be able to make $70 to $80 on those bobbleheads. Sometimes people don’t always know the value of their items so it definitely pays to always search. And in the third way I also source is by using Graigslist, Facebook Market Place and Next Door. You can toggle the search bar to see if the items are free or paid. I check the free section. I’ve found free computer books, free cologne bottles that I can easily flip for $35 to $40. So there are definitely a lot more places to source other than thrift stores. But for me, thrift stores are my favorite right now.

Tom: Well, it sounds like you got a system down pat so that that helps. One of the things I was thinking about on sites like eBay is where you get these lots if you’re willing to have the inventory (and maybe get stuck with a few losers in there) where you might buy 100 of some collection or something and piece them out, selling them individually for a higher price.

Jason: If I were heavy into clothes, I could make a killing doing that. But the issue for me is, clothes can be lucrative but it’s hard because you’ve got to do a lot of research. There are thousands of brands, thousands of sizes out there. I don’t know… clothes just don’t do it for me.

Tom: I also like how you mentioned about getting free items because I think there are some things in my garage, I would happily get rid of for free just to just get rid of them. Sometimes it’s too much hassle to get list though and have to deal with a bunch of people that don’t want to come look at it. I had sold a bunch of video games before and I found the best value I was getting was selling them through a local Facebook group. It was basically a “buy-and-sell” videogame group. And because of that, these people understood the value. There was a collectability to it. Have you ever sold somewhere else? We’ve talked about how you sourced from different ways, but have you tried selling outside of eBay?

Jason: Believe it or not, I have items listed on seven different websites; eBay, McCarry, Poshmark, OfferUp, Facebook Marketplace, Craigslist, Next Door. There was another site called, Let Go, but it merged with OfferUp last month. That’s literally where I sell the majority of my items are right now. Everything is on eBay and I’ll cross-post to different sites where I feel like I can get them to sell. For example, jerseys and shoes will be cross posted on McCarry and Poshmark. Bigger items such as books will be cross posted onto Facebook Marketplace or Craigslist.

Tom: Things like books and CDs, have you ever tried selling them on Amazon? I know there’s a whole listing process for that which seems a little daunting.

Jason: Yeah, you said it right there, it does seem a little bit daunting. And I don’t really feel like learning a new thing right now—another platform. Because I believe that there you can make money with Amazon but just the small research that I’ve done, you’ve got to pay so much and have so many items. And from what I saw, they take out more than eBay. I’m trying to make money because I’m still in the process of paying off debt. I’m trying to make money instead of giving more to another platform.

Tom: I had mentioned to you previously that I’ve got this this huge CD collection. It’s been sitting in boxes for most of 20 years, certainly 15 years. I just don’t know what to do with it. I’ve looked into this Amazon thing and it looked too tough to just to turn around and sell CDs for 50 cents or a dollar. So, yeah, I might need to look at something like eBay to try to sell them. One service I like the look of, but we don’t have available here in Canada is, Declutter.

Jason: Declutter, I was just about to say that.

Tom: Granted, you’re not getting the best value there. But to be able to just ship off a box and tell them to sell the stuff… I’ve talked to the people at Declutter asking them to please come to Canada. I will be customer number one to sell all of these CDs that are sitting in boxes—many hundreds of CDs.

Jason: I guarantee you probably have some that are worth a lot of money, too.

Tom: Yeah, well, that’s just it, too. There’s certainly some super rare ones, some local bands, some bootlegs. But then again, for me to do it, I’ve got to sit down and go through all of these. And for those ones that may have a premium to them where they’re maybe worth $50 or something, I know a lot of them are $1 and underpriced for your regular CDs.

Jason: Then it really wouldn’t be worth doing out of research for that.

Tom: Yeah, that’s I’m thinking so I wish something like Declutter would come to Canada. That would solve all my problems for whatever price. It’s kind of like the stuff in my garage that I’d be happy to get rid of for free, I’d be happy to get rid of these for just some kind of fair value—just to get them off my hands. You mentioned that you started this just as a way to help your finances. I’m a huge fan of side hustles to get that under control. Sometimes the day job just doesn’t do it. You need that little something on top. Did you try other side hustles before you locked in on this one?

Jason: Yeah, I tried a few side hustles. I’ve tried doing freelance writing. I’ve tried doing freelance tasking on UpWork. I’m not going to lie, you can make a lot of money doing freelance writing. But at the end of the day, while I was doing freelance writing, I was neglecting my site and other side hustles. Then I started to dread writing. I would wake up on a Saturday morning thinking, “Crap, I’m going to be writing for six hours!” At the time I was still working a full-time job. I got to thinking, “Man, I’ve got to write for six hours, what am I going to do for the rest of my weekend?” I didn’t want to start my weekend at 4:00 am on a Saturday. I guess the universe hired me so I ended up losing all of my freelance clients in a 6-week timeframe. I just took that as a lesson. I figured I could start back pitching people or focus on the other side hustles I really liked. That’s when I started taking eBay a little bit more serious. And from there, many things have just been going up ever since then.

Tom: It sounds like something where you’ve got a little more freedom of time. You mentioned freelance writing. And yes, you’re committed to provide articles on certain dates. But with this, it’s something where you can decide if you’re going to spend an entire day doing this one week. While another time you’re just going to spend an evening . And maybe even one week you’ll just take it off. I’ve been a big fan of things like Uber for the same reason—just the idea that you can turn on your app when you’ve got a couple free hours and hopefully make some money doing it. I assume it’s the same with you. You can see how your day goes and fit it in?

Jason: Correct. It’s crazy that you brought up Uber. I was doing Uber Eats before the pandemic started. I would do 4 or 5 hours a week or something just to test it out to see if I could make any extra money. And it’s definitely lucrative if you put the time into it. But I haven’t done it since the pandemic started because I want to be safe than sorry right now.

Tom: This is another great point you’ve brought up. I think the whole COVID pandemic has really opened people up to some of these things, like one. One, it’s just nicer to make a little extra money because people are concerned they may lose their job (or have lost their job). People see it from that career standpoint, but it’s also the fact that some of these things are online. People are kind of waking up to this idea that they can make extra money online. We’re both doing it. I have my blog. You’ve got the eBay thing and your blog. I think a lot more people are going to start to come into this space with all these different online apps and services. And they’ll find their own way to make money.

Jason: And it’s a good thing because at the end, I like it when people realize that you can’t count on a job because you could be let go at any moment. I was let go right when the pandemic started. So things can happen but you don’t have to feel bad or sorry about yourself. You just have to find that side hustle and get to work.

Tom: Yes, it gives you a little something extra if you’re living paycheck-to-paycheck. It’s this little something extra. That’s how you pay off your debts and get that emergency fund. Maybe it doesn’t replace your income completely but it’s something. It’s padding, some breathing room. If someone wants to get into a side hustle like this, selling online, flipping items, where should they get started? I’m sure you’ve got some resources. But just in general, what steps do they need to take to get going on this?

Jason: What I would tell people is, the first thing they need to do is just get started. I’ve talked to so many people who are interested in selling on eBay or McCarry or one of these other platforms and I contact them in a couple of weeks and ask them how their journey is going. I ask how many items they’ve listed, how many sales they’ve had to date. Some of them say, “I just don’t know, man. I’m nervous.” There is no reason to be nervous. It’s free to create an account with eBay. You get 50 free listings per month so you don’t need a store. All you have to do it go to the eBay website, click sign in, put in some information and you can get started. That’s the first thing I would tell people to do. Second, another big question I get all the time is, “I don’t know what items to sell. What works?” I tell people to start with what they know. Like I said earlier, I’m a big sports fan—a huge sports fan so I started with sports items; jerseys, Michael Jordan tennis shoes and bobbleheads. Then I branched out from there. So I’d tell people to start with they know. The next thing is, once they realize that eBay is for them and they’re making some money, instead of having 5 listings, try to double it to 10. And from 10, go to 20. Make sure you’re taking a decent number of pictures too. Some people may take 3 pictures, post it and put on a little title and description. Then they get mad when the item doesn’t sell. Unfortunately, eBay doesn’t work like that. It may take a couple weeks for items sell and that’s fine because that’s money you have coming in, regardless. A lot of people think things will sell in 6 to 24 hours and that’s not always the case. I tell people in my Facebook group and friends who sell that this is a long game. Your stuff will stay up but you’ve just got to be a little bit patient with it.

Tom: I like the idea of taking a bunch pictures because I know me as a buyer, if I were to go on eBay, especially being used items, I want to see that product from every angle. I want to know if there’s a scratch or a hole or something like that.

Jason: Exactly. Grab up to 12l pictures for each item you’re selling. I try to make sure that I have at least 9 pictures. The majority of my items are used so I want a potential buyer to see the front, the back and the sides of the item. Also, in the description, if the item has a hole in it, or a scuff mark, I include that information because, believe it or not, there are a lot of people who restore items and can refresh things so they will buy it, fix it up and either keep it for themselves or resell it. So, I’m always honest in my listings. And you wouldn’t believe some of the crap I sell because of that.

Tom: You mentioned the beat-up Jordan’s that still sold right away?

Jason: Those Jordan’s were horrible. They were at least 8 years and I was shocked that I made $40 off those shoes.

Tom: I’ve mentioned all the junk I’ve got that I still need to get rid of from bad spending decisions in the past. Would it be easy for a lot of people to start with that? That’s sort of like instant profit, right? I mean, the spending has come and gone but they could sell some stuff and free up some space in their own house, make money by just getting started.

Jason: I would definitely start with some old items. If I was a beginner just starting and had some items, whether they were in the closet or under the bed, go through those items and make sure they’re clean and then list them on eBay and other sites such like Craigslist and Facebook Marketplace. You’ll be surprised how many people will contact you if you’ve got some good items. You could have $5 or $10 in no time.

Tom: Thanks for running us through this. I think it’s a rather unique side hustle. I don’t know other people doing this eBay flipping and I think it’s one of the great options out there for people. I think everybody should try everything to see where they fit in. Can you let people know where they can find you online?

Jason: Yes. You find me @mymoneychronicles on Instagram. On Twitter @money_chronicle. And I’m also on Pinterest, My Money Chronicles. If you’re on Facebook I do have a Facebook group called, My Money Chronicles – Inner Circle where I literally talk about eBay, Poshmark, Flip It and other side hustles. I like to say I’m like a “no shame zone” where people can ask any questions they want because at the end of the day, it’s all about learning. And once you learn, you’ll be able to make more money and you can help other people learn as well.

Tom: That’s great. I think people should check out Facebook groups because there are Facebook groups that support just about anything, you’re trying to do so you don’t have to do this by yourself.

Jason: Definitely. In my group, if I’m not there to answer questions, maybe one of the other administrators are, or some of the group members. Side hustlers in my group make some decent money, too.

Tom: Awesome. Thanks for being on the show.

Jason: No problem, Tom. Thank you very much for having me.

Thank you, Jason, for explaining how flipping items on eBay works and for showing what’s possible with this very interesting side hustle. You can find the show notes for this episode at The Canadian Financial Summit starts October 15th. This is a virtual event featuring many of Canada’s top experts in personal finance and investment, including yours truly. If you’d like free tickets to the entire summit, head over to to sign up today. I’m looking forward to having you back here next week when Marcus Garrett will be on the show to discuss his four-step, debt plan. See you then.

In most thrift stores, I go straight to the shoes first. I check out the shoe section, and then from there I look into clothes, then the DVD/ video game section, and toys. The reason I do that is that there’s not many shoes. It’s the easiest section to look in. - Jason Butler Click to Tweet