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Transitioning From Side-Gig Success to Quitting Your Job, with Steve Chou

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.

Steve Chou and his wife started an online business that allowed his wife to quit her job. Before long, Steve’s own blog also became a success. Eventually, he left his full-time job, and today both businesses have become highly successful.

In this episode, Steve explains why he stayed at his full-time job as long as he did, and provides some advice for anyone wanting to start an online business or convert their side hustle to a full-time gig.

Find out why Steve doesn’t recommend quitting your job to start a business, and why he thinks your online business needs to sell something.

Did you know? Our sponsor, Wealthsimple, offers a free review of your investment portfolio. They’ll help you set financial goals, suggest ways to lower your investment fees, and the amount of tax you pay. Head over to Wealthsimple to get started today!

Episode Summary

  • Steve explains how his wife’s tears led to their first business launch.
  • How Steve and his wife replaced her six-figure income in a year.
  • Blogging is the wrong business model if you want to make money fast.
  • Why your online business needs to sell something.
  • Steve shares advice on juggling family, career, and your side hustle
  • Why you shouldn’t quit your job when you start your business.
  • Steve takes us through the many businesses he owns today.
Read transcript

Steve Chou and his wife started an online business so his wife could quit her job. Then Steve’s own blog (appropriately named) My Wife Quit Her Job, also became a success. In fact, both businesses did so well that they were making much more online than they did at their day jobs. Today we dive into why he stayed at his job as long as he did and what things are like now that he’s quit to focus on his family and multiple businesses.

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

Our sponsor Wealthsimple offers a free portfolio review. They’ll review your investments, how much debt you have and whether you’re saving enough. Weathsimple also helps to set goals and suggests ways to help lower your fees and how much you pay in tax. Head over to today. Let’s chat with Steve…

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

Steve: Hey, glad to be here, Tom.

Tom: So I wanted to ask you today because dealing with you a lot in the past, I know there was a point where you were still working at your job and struggling with balance between really enjoying your work and wanting to improve your business. But before we get to that let’s go all the way back to the beginning of all this. Your wife, Jen, quit her job which leads to the name of your blog but can you tell me a bit about how that came about with your first business?

Steve: The reason we started that first business which was an e-commerce store selling handkerchiefs is because my wife wanted to stay home with our kids. It was our first child and we both kind of agreed that it made sense to have someone stay at home. The problem is, where we live pretty much requires two incomes to get a good house in a good school district. We were thinking long-term at that point. At the time my wife was making $100,000 and we needed a way to replace her salary since she was staying at home.

Tom: So how did the idea come about for this business? One of the topics we like to talk about here is different ways to make money and I know you have a pretty unique story on how that business started.

Steve: Yeah, it actually started when we got married. My wife knew she was going to cry and we had spent all this money on photography so she didn’t want to been seen using ratty tissues to dry her tears. We looked all over the place for handkerchiefs but we couldn’t find any in the US. Then we found this factory in China where we ended up buying a whole bunch of them. We used them for the wedding and sold the rest on eBay where they ended up selling like hotcakes. When it came time to start our business we got back in touch with our vendor and launched our store.

Tom: And, I believe she was able to replace her income the first year, right?

Steve: That’s correct. That was not actually the plan though. We would have been happy with just $60,000 but it just kind of took off.

Tom: Aside from your help on that business, your first side-hustle, you were still working at your job and you started this blog, My Wife Quit Her Job. Can you tell me why you started that and how that helped with income as well?

Steve: I started that after reading Steve Pavlina’s blog. I don’t know if you’re familiar with that. He wrote this one post on how to make your first love dollar. At that time he was making $4,000 a day in AdSense. This is back in their heyday—AdSense. And I figured I could do that too. So I just started documenting my store on the blog and it started gaining an audience. I started making a little trickle of AdSense here there but I just kind of made it part of my routine. I just wrote once a week and things started to snowball over time.

Tom: Okay. So the success of this blog continued to increase and you were still working. In our own private conversations I know that you had to struggle with the balance between what you wanted to do going forward.

Steve: I remember struggling because I was trying to write every single day of the week (in the very beginning of the blog) while working a full time job and helping out with the store. But once I dropped down to once a week writing—and writing on a blog these days is not a volume game. It’s more about quality so it got a lot easier. I actually didn’t struggle with the work life balance once I dropped down to less writing.

Tom: But you were also unsure of when you were ready to quit. I know we were talking about that for awhile.

Steve: Yeah, we were. I actually never wanted to quit, mainly because I worked at a high-tech job with a whole bunch of smart people, people smarter than myself. They all had PHDs from IT, Princeton, Stanford. And I just really liked the idea of working on a project with a team. I struggled with quitting because I didn’t want to quit. Ultimately, I had a sweet deal towards the end where I was just working two days a week and I negotiated where I could work on my own stuff at work. That arrangement was really ideal because I had the best of both worlds. But, if it weren’t for a few things that happened to my company, I might actually still be working today, even though my side-hustle made 10 times more than when I was making at the day job.

Tom: That’s one thing I’ve always found interesting is you’ve made so much more on these side-hustles and they’re so much more than your day job, so yeah, you obviously liked still working there, right?

Steve: Yeah. My wife actually did not like her job so we had to get her out of there really quick and the business was a good solution for that. For me, I was just trying to make some side money with the blog which ended up blowing up after three years, I would say. It took awhile for it to blow up but ended up doing that. I had no intention of ever actually quitting my job really.

Tom: I think a lot of bloggers start out that way. It is half hobby, half side income and it’s not normally the plan. Maybe more nowadays. I think a lot of people want to start a blog just so they can quit their job.

Steve: I don’t know if the blog is the right way to go because it takes a long time. You’ve got to be really, really patient. And, since every company is doing content-marketing these days, I’d say it’s a lot harder today.

Tom: Yeah, we had an episode with Philip Taylor where he said, “Out of all the different ways people can make money, blogging is one of the worst.” Even back in the day, just like me, you could go months to half a year—even up to a year for some people without making a dollar so it’s not something you can just hop into and make money.

Steve: I will say this though… once it does take off I think it has a lot of staying power. Once you have an audience and a fan base it gets a lot easier. You have to get over that really hard first hump.

Tom: You have to truly do it on passion before you can actually make money from that.

Steve: Yeah, for sure.

Tom: Okay, so you’re at the point where you’re quitting your job. How did that benefit your business?

Steve: I’ll be honest with you. When I quit my job, I actually worked the same number of hours on my businesses. It’s just that the hours I was working for my job I now spend on my kids. Right now, during this interview, my kids are actually downstairs and I’m probably just going to hang out with them afterward. I can just kind of time shift my other stuff.

Tom: So it is more of a lifestyle upgrade?

Steve: Originally I thought, wow… Now I have 40 hours of work for my businesses and I’m going to be unstoppable but I found I can’t really do eight hours of sustained work in a day.

Tom: I’ve heard that before too, that a lot of people just aren’t wired to work eight hours. I think I read it was 4 hours or something like that.

Steve: Like the four-hour work-week?

Tom: Well, no. It’s more like the four-hour work day. The idea is that’s your most efficient time. You find that perfect four hours and it may not be 8:00 in the morning. After that, people aren’t really working. If someone’s at a career they’re not really putting in eight hours a day at work. They’re hanging out at the water cooler and stuff. And, you need that time. It’s not that it’s not part of the overall picture.

Steve: There are days where I work straight through, sometimes 12 hours without even eating. But those times are kind of rare. It’s only if I’m really into something and I’m in the zone. But for the most part, you’re right, it’s probably around four hours a day. I work until lunch time.

Tom: Yeah. And that seems so much more efficient for operating a business. It does benefit your business in a way because those days that you do want to do that 12 hours—just because of momentum and hopeful not just because of deadlines, but because you’re actually working through something.

Steve: It’s funny, when I had that job where I could work on my own stuff at the office I used to crank it out because I just closed the door. I was in a different environment and I had all this time. There was peace and quiet. It was nice.

Tom: Okay, so we covered beginning to end with your story. If someone’s looking for a way to do something similar like maybe start a business that they hope to grow, what steps should they take?

Steve: I think it just depends on your time frames, really. I would say if you want to make money sooner rather than later you have to sell something. An e-commerce store makes a lot of sense because you’re selling physical products and you’re exchanging money. If you have a longer term timeframe, between three to five years, maybe blogging might be a better choice because you’re kind of slowly building up an audience who really trusts everything that you recommend and you could turn that into a more low-energy business like selling digital products or doing affiliate marketing for that matter. So, it really it depends on your goals. If you need money right away like we did when we had our first child, selling physical products is probably the way to go.

Tom: You’re in this area a lot. Is there a lot of room still for e-commerce? I know Amazon’s been big but that’s also helping when you’re selling on Amazon, of course, too but is there still room for entry there?

Steve: Yeah, I mean everyone asks me that question about every single type of business. The answer is always yes, to everything. Things always get a little bit harder. You just have to find more creative ways of improving. For example, Tom, I’ve been blogging for almost a decade now. You’ve got to worry about new social media rules, new SEO stuff—I mean, it’s a constantly evolving process that you just have to learn about. And there’s always room to grow but you have to also constantly improve.

Tom: I know nothing about the e-commerce side but I suppose it’s no different than blogging?

Steve: It’s the same exact thing.

Tom: If you can bring something unique to it that might give you a sort of a little niche where you can—

Steve: Yeah, that’s the key. The key is really just to stand out. As long as you are doing something that allows your business stand out you’ll probably be successful. The people that tend to fail are the people that just put up these cookie-cutter things or they don’t have a strong value position. Those businesses are going to die.

Tom: Have you ever had someone try to copy your business, either one of them?

Steve: I have. Someone started Hummingbird Linens and that died off in less than six months.

Tom: That’s a perfect example. What else can someone do on the career side? If they’re trying to build a side business and also managing a career— you’ve always been good at making that all work. Plus you’ve had kids. You were always in the same exact position as me where you’re trying to juggle these three things of family, career and side hustle. Any advice for that?

Steve: Back when I was working full time and working on the side hustles I think the key thing to realize is that slow and steady is better than bursting chunks. What I would do is set aside one or two hours after I came home from work to just work on the business. I would just do that every day. If you try to do everything all at once you’ll end up burning yourself out. But if you’re on a schedule it just becomes part of your routine and you don’t even think about it anymore. Before you know it, months have passed by and you’ve made a tremendous amount of progress.

Tom: Yeah, so just keep taking those steps. Mine was similar too. I worked my day job, spent my time with my family. Then when the kids are going to sleep it was business time—time to get in there and start working.

Steve: You just have to be willing to put a couple of extra hours in at night or on the weekends. You’ve got to make a few sacrifices.

Tom: But it’s so much more efficient than someone that spends all their evening watching TV and says they don’t have any time to do this extra stuff. Is it just that they have to find the time?

Steve: Yeah… I mean, I waste a lot of time. I still do. Back then I wasted even more time. It’s just a matter of finding those things you’re doing that really don’t have an intrinsic value. I classify watching TV as one of those things so TV is probably one of the easiest things to cut out. Just bumming around doing nothing is another thing. I don’t know… I just used to waste a lot of time browsing sites that really didn’t have any value.

Tom: Yeah, it’s tough when you’re working on an online business because you need to be on social media and things like that. But it seems you can fall down the hole and before you know it you’ve wasted an hour on Twitter or YouTube or something.

Steve: Facebook and YouTube are probably the biggest time sucks. There is plug-ins that will just remove your feed altogether so you’re not tempted.

Tom: I’ve heard that. I haven’t been brave enough to try that because I still like the addiction of seeing everything updated and everything.

Steve: So, never complain to me Tom, that you never have enough time because I know how you spend it.

Tom: Yeah, I’ll admit I’m not as productive as I’d like to be. People always ask me how I do all this stuff but I lose a lot of time for those same reasons. It is easy to get distracted and procrastinate. Why work on your business when you can watch a bunch of videos on YouTube. At least with TV it’s a lot easier to cut out because at least with TV it’s more of a physical thing where you’re sitting down front of a TV and you’re watching it. With social media, I try to go on there as part of my business and then I get lost.

Steve: Yeah, totally.

Tom: Okay, are there any more tips you could give, especially toward this idea of balancing both kinds of work and family and everything?

Steve: I don’t think you should quit your job when you’re starting your business. Some people advise you just go “whole hog” and quit. One thing that (at least for me is) I don’t like, is having pressure to make money right away. And that’s what quitting your job would tend to do. The reason I say that is because you don’t want to be making business decisions based on money. For example, you want to go with a cheaper service because you want to save money. You want to make the right decisions. You want to have a nest egg in place. You either have to have a nest egg or you need to keep working your full time job. If you want to be making the right decisions that will allow your business to be successful, you don’t want a cheap out, basically.

Tom: Exactly, that’s great. Can you let everyone know where they can find you online?

Steve: Yes. So if you want to find out more about the businesses that run my blog at is basically a diary of all my business exploits. And if you’re going to get married I can hook you up with some handkerchiefs over at

Tom: You also have a course for someone if they’re looking to get into the e-commerce side?

Steve: Yeah, I run a training class over I also run an annual conference for e-commerce sellers at And, I also run a podcast called, My Wife Quit Her Job where I just kind of bring on guests and we talk about business.

Tom: Sounds like you need more things to do.

Steve: Actually, I’ve got two more things. We recently launched a new business called, Go Brand Win. It’s like a group give away service if you want to build your e-mail list fast. And, most recently, I just announced a brand new show called, Five Minute Pitch. It’s basically a shark tank sort of show. We’re hiring a professional video crew to put on the show so it should be fun.

Tom: That’s great. Thanks for being on the show.

Steve: Thanks for having me, Tom.

Thanks to Steve for sharing his entrepreneurial journey. Thank you for listening each week because it’s what keeps me motivated to keep finding unique guests to come on the show and share what they know. You can find show notes for this episode at If you can think of someone looking to get into e-commerce, please share this episode with them. It will help them greatly on their path to creating an online store and I’m always happy to have more listeners join the show.

'I was just trying to make some side money with the blog, and it ended up blowing up after about three years….starting out, I had no intention of quitting my job.' - Steve Chou Click to Tweet