Building a portfolio of sides hustles

How Jamie Northrup took advantage of the compounding effect

Feb 26, 2024

Jamie Northrup started building side hustles at 13 by trading hockey cards. Once he was laid off from his job in 2023, he decided to go all in on his newsletter, Minimalist Hustler. He’s so perseverant. It was inspiring talking to him about his journey. He’s built so many side hustles!

You can find Jamie on Twitter and Medium. Also, check out his newsletter.

Let’s get started!

Navigating full-time employment and side hustles

Kenny Alami: You've been doing a bunch of side hustles since 13. Right. You eventually got a job but still kept going with your side hustle. How come you didn't go full time on your side hustle sooner? Was there any reason there that you didn't take that decision?

Jamie Northrup: There's been times where I've thought about it before. I had my own web consulting agency where we managed websites, emails, and design websites, and that worked really well from the income side of things. There was a point where it came really close where I was going to be going all in on this. But it didn't feel right to me. I'm happy I didn't because, honestly, I got fed up with it. I tell people all the time they have to follow what they're passionate about, or else it's just the same thing as getting a 9-5.

Instead of having your boss, you have all your customers as your bosses, and it's horrible. So, I had a few issues with some customers, which opened my eyes and made me rethink things. That's where I transitioned to what I'm doing now. What I'm doing now is a slow process, but it's a process that works for me. I could have probably left a year ago, but I was able to manage my 9-5, which was quite flexible at the time with it, so there was no reason for me to leave. In August of this year, they gave me a package. They laid off quite a bit of people and they gave me a package. So it worked out for the best.

I got some extra money, and now I'm full-time on it. I’m not looking to go back anywhere. I'm not saying I'll never take another job. I haven't looked for another job. Some people have tried to approach me. I did apply for one that was in actually the newsletter space, because I'm very interested in the newsletter space right now. If I could get a job that helps me do what I enjoy doing, then I'm for it. But if not, I'm good with it.

I like having the side hustles stay as side hustles. There's less stress about it because it's not all you're relying on. Although I'm at the point where I have 11 of them, so there are 11 different income streams, and some are higher than others. Some go high, then they go low. They balance each other out. I love having a lot of different things and it takes away from the stress of heavily investing in one.

Kenny: How long were you at your previous job?

Jamie: Before I got laid off in August 2023, I was at the same job for almost 20 years. Most of the side hustles I had in my adult life were while I had this job. I’ve had other jobs before, but this was the longest one.

Kenny: Was your employer open to the idea of you trying many things on the side? How did that go?

Jamie: I never asked. They never mentioned it. Although, there was a problem one time. It was based on LinkedIn, and this was around ten years ago. I was using LinkedIn to promote a side hustle related to Twitter. The vice president of our company at the time came to see me and said, “Look, I don't mind you having these side hustles, but you can't represent our company on a website where you're representing these side hustles. Either you remove the company from your profile or remove the other.”

Kenny: Oh, wow.

Jamie: I made the choice to keep the company name because I wasn't sure what he would do if I did the reverse. Actually, before I started Minimalist Hustler, I decided to deactivate my LinkedIn. It was deactivated until I got laid off.

Kenny: Oh, man. How did that feel for you? Did that start turning some gears in your mind when that happened?

Jamie: LinkedIn was a distraction more than anything else because I had built my profile 99% around my 9-5. Every week, there would be 2-3 people trying to offer me jobs in my industry, and I was not interested. So, I shut it down. I never really had a desire to bring it back, even after I started Minimalist Hustler, because I was doing pretty well on Twitter and then on Medium.

Kenny: Not too much of a hindrance to remove in the end. Sometimes, people find that a big downside of having a job, and they feel like they have to go behind their employer’s back.

Jamie: Even before COVID happened, I had been working at home. I worked at home for two and a half years. Then it was 90% at home and 10% at the office. It was very flexible regarding time and location, so I couldn't complain. They didn't give me a reason to want to go behind their backs or anything like that. I never spoke about it to them, but if they asked me, I would tell them the truth.

Jamie: If they ever told me, you must pick us or the side hustles. I would have picked the side hustles at that point. But I'm happy they didn't because if they did at that point, I think I'd be stuck in my agency and not have even built a minimalist hustle at all, which would have been disappointing.

Kenny: Fascinating how people sometimes feel stuck in their jobs, but then being stuck in your own agency or business doesn't seem to be very fun either.

Jamie: That's it. When you look at it, if you have just a job, I find it's much easier to get unstuck. Either go get another job or do something else. But if you've built a business and that's your income, you can't just say, “Tomorrow, I'm going to shut down.” When I decided to shut down my consulting agency, it took almost two years after I took the decision and got rid of my last customer. You have to get them options and offboard them properly.

But if I were relying only on that income, I wouldn't have been able to do that because then where would my income come from?

Kenny: 2 years to finish fulfilling those contracts and offboarding them?

Jamie: It wasn't just designing their websites. We were managing their websites and their emails. We had to get that transferred to different suppliers for them. A lot of them had no clue. They had never dealt with anybody else before. That's why I had to help them transition out.

Kenny: During those 20 years working for this company, were you always doing something on the side? Was your agency something you started initially, or at what point did you start that?

Jamie: I always had stuff on the side. But before I got this job, I started making websites for myself. I had a lot of blogs with AdSense. Slowly, as word got out, people were asking, “Oh, you make websites. Can you make me one? Can you make me one?” I launched in 2006 officially and I started designing websites for other people while I had my last job.

Family life and side hustles

Kenny: You had a bunch of side hustle, the agency and your full-time job. Although in 2006, you didn't have kids. How was it for you to manage your time and time spent with your family? How did you juggle it all? That sounds like a lot of work.

Jamie: It is. There are a few things. One, my job was very flexible, so it was easy to get a lot of stuff done in between tasks. I didn't have kids like you said. I had built up 2 or 3 dozen affiliate marketing websites, and there were three making money consistently. As soon as my first son was born, I stopped working on them, saying, I'll get back to it. Then it was just too busy and I never got back to it. They just died out. They still made money for about three years until they completely folded over.

Then, my second son was born. At that point, it was time priority became a thing. It was my customers’ websites and nothing else for a good 4-5 years. Once things settled down again, that's when I started doing stuff on the side. But even then, it was mostly client work most of the time. Because there was so much of it. I didn't have as much time to follow the paths I typically wanted to follow regarding side hustles and making money online.

Until December 209, I made it a New Year's resolution, which I don't often do, but I made it a resolution to try and find ways to make money. I don't remember exactly how I worded it, but it was something like how to make money with as little things as possible.

For example, I started trying to deliver food for Uber, where you just have your phone in your car, and that's all you need.

It was in February of that year that I registered the Minimalist Hustler domain. I came up with this idea to try and help people make money with as little things as possible. You don't need special skills, you don't need degrees, you don't need money. You just need specific little things, and you can go.

Kenny: What does your schedule look like?

Jamie: It's hard to disconnect sometimes, especially when you're in what I call “build mode.” When you're really into it, it's hard to be like, “Okay, I got to stop now because I got to go spend time with family or go do other activities.” You want to keep building because you don't want to lose that momentum, but it's important to have a good balance.

In November 2023, I did a crazy challenge that screwed up that balance big time. For the most part, what I'll try and do is time my work time with their schedule. My wife works 9 to 5, Monday to Friday, so that's not a problem. Usually, the kids are in school. The bus leaves here at 7:15, and they come back at 3:15.

What I'll try and do is work from 715 when they leave until 315. They come back. Then I'll take them skating because there's usually an hour of free skating at the arena. So I'll take them ice skating for an hour, and depending on what I have going on, that'll be it. I also stop for lunch and I'll run errands, depending on what needs to be done, too, during the day.

Except for November. I had this insane challenge I wanted to do, and I did it, but it took a lot more hours. There were many nights working till midnight and 1 AM. It was challenging. Although, normally I try and stick to 7:15 to 3:15. That's more than enough to get everything done.

How it all started for Jamie

Kenny: How did the Minimalist Hustler idea emerge? It seems like you were doing mostly client work or work for others at the time. It didn’t seem like you controlled what you were working on.

Jamie: There were incidents with some customers from my consulting agency. I mean, there were issues for 20 years with customers at my regular job. I thought, “I'd like to find a way where I don't necessarily have customers.” That's when I started searching for “How can you make money without having customers?” Which is a weird thing to say, but I found more and more options. Then I realized it's not necessarily about having no customers, but it's about being very transactional with the work. When you do food delivery for Uber, for example, you have no customers. The customers are Uber's customers. The restaurants are customers of Uber. Nobody's a customer of yours. If there's any problem with a restaurant, a customer or if you have a problem, call Uber. That's it.

When I started doing Print on Demand, I would use Redbubble at the time and Amazon Merch. If there's a problem with the product, they don't contact you. They deal with Redbubble or Amazon. Nothing to do with you. After that, I discovered Amazon KDP. Again, it's the same thing. You write books. People buy the books. If they don't like it and there's a problem. They deal with Amazon you have nothing to do with it. In those scenarios, there are no customers.

Then, I started creating digital products. Very low-end digital products at first, and I realize. Yes, I have customers for these digital products, but the second you have an unhappy customer, you just refund them, and it's over.

It's not like you're building a website or managing their emails, and they're unhappy with something. Then, you have to figure out how to fix it. Here, it's like, “You bought this template or ebook. You don't like it? Here's your money back. Onto the next one.” It didn't cost you anything. It doesn't really matter.

Finding things that are transactional on an individual basis was very key to me. Over time, I developed relationships with customers through Minimalist Hustler. The big difference is, and again, it comes back to passion, is I love what I do.

It shows when I do it that I love it. When I deal with the people who become my customers or long-term relationships, I love interacting with them. There's no stress or upset customers or anything like that. It's very enjoyable work. It's definitely not the easiest or quickest to scale. It takes time. But to me, putting enjoyment above income or growth is very important. That's one of the basis behind Minimalist Hustler.

Kenny: Many people experience that they don't want to deal with customers. I sometimes have this feeling too where I’m thinking “Wouldn’t it be nice not to deal with any customers?” Although you still need someone to buy whatever you’re producing. You nailed it with your point. It’s about enjoying interacting with your customers and finding this sweet spot. The other part of the equation is if you want the least amount of interaction, you’ll need a smaller product because the more expensive the product, the more interactions with customers throughout the sales process.

Jamie: In theory, yeah. There are some exceptions. You could get high-ticket items, but you have to be comfortable refunding the customer if there is a problem.

To me, if I'm building something and selling it multiple times, I've already built it, and I'm already selling it multiple times. So, refunding is not necessarily a hard issue for me. It's also not hard to refund. Whether it's $4, $10, $100, or $1,000, it's still a digital product. Yes, you've definitely put more time and effort into the $1,000 product than the $4 product. But at the end of the day, each sale is still profit, whether your cost is already predetermined.

It's not like you're selling a physical item or you're selling something that's requiring more of your time, as a typical service would. Then you're losing your time if you refund. Your time has already been invested, and now you're just reaping whatever you can get, and if there are refunds along the way, then so be it.

Managing lack of results and consistency

Kenny: The layoff wasn't that much of a low point because you already had some stuff going on. But in that whole journey, what was one of your biggest struggles?

Jamie: The moment I realized the consulting wasn't for me, it was a struggle where I knew it was not for me, but what will I do now? I never wanted or meant to be a 9-5 person for my whole life. My job had nothing to do with what I studied at university. But it was a job I got when I was 21 years old, and I stuck it out. The low point was trying to figure out what I would do. Once I figured out what I wanted to do with the Minimalist Hustler approach, then the question was, “Will this even work? How long is this going to take?”

After the first six months or so, there was a point where I thought, “Maybe this is not going to work and I should try something else.” But I kept going anyway, and I made changes along the way about how I was doing things and what I was doing. But the end goal was the same, and I'm happy I stuck with it. When I think back to many of the things I did before the consulting agency, or even some that I did during, if I had stuck with them longer, they would have given much more fruit than I could imagine. It was hard at points, but in the end, it was worth it.

Kenny: What do you think? Was it maybe the lack of results? That was hard because I understand that you kind of felt stuck or you needed a way out, and then you found that kind of way out, but then trying it out and maybe seeing that it wasn't working as you expected, was that the hard part of it?

Jamie: Yeah, definitely. One of my top income streams now, and it's been my top income stream for a year and a half, has been my books on Amazon KDP. So, I have over 500 books published on Amazon KDP.

Kenny: Wow.

Jamie: Out of the 500, 30-40 have ever even sold one copy. Out of that 30-40, there are only 7-8 that sell on a somewhat regular basis. So it's hard to imagine when you're in that situation. You're working on these things between 20 to 50 hours depending on the week, and you're getting sometimes $10-40 a week. It's hard to stay motivated and say, will this really pay off? What I tell people is if I look at my life today and the number of hours I put into Minimalist Hustler today, it's the same amount of hours depending on the week that I did at the beginning.

In the first year, I probably didn't even make money. I probably lost money, but I might have made $100 or $200. Then, if you look at it now for the same effort, I will break almost $100,000 for doing the same work. It's sticking with it through the hard part and keep on going and going. I'm at 7000 subscribers now, but when I started in 2023, I don't even think I was at 2000. It compounds with time. My income basically doubled. 2.4 times more income this year than last year. I expect next year not necessarily to be 2.4 times. I'm expecting it to honestly be probably 3-4 times what I did in 2023 because of the compound effect.

But it's hard in the early days to believe in that. But if you get 1% better every day, by the end of the year, you're 37 times better, like James Clear talks about. If you think about it, it seems simple. Let's say you take something more concrete. Let's say you say I could do 10 push-ups today without stopping. If you did 1% more every day, at the end of the year, you'd be able to do 370 push-ups. Now try and think about 370 push-ups, knowing that you can only do ten today. Really believe that you can do 370 in a year.

Jamie: I didn’t believe that I would be able to do 37 times more. But the thing is that you're going to do 10 today, and then tomorrow, you're still going to do 10. Then you're going to do 11 and 12 eventually. It will go up faster from there, and you won't even realize it. There is a good chance that you'll be able to do 370 if you really stick with it for a whole.

Jamie: You have to stick through the parts where it looks like there are no results. It looks like you're not going anywhere. It looks like you're just doing the same thing repeatedly. But it will lead somewhere. The 2-3 months are easy. It's the next 3 months to 1-2 years. That is where it can be hard. Because if I look at the amount of money I made last year for the amount of hours I'm putting into this, it's still not worth it. Now, it's starting to be worth it. Now, if the curve keeps going, then it'll be way more than ever worth it the year after and a year after. It's a combination of all that. It's hard when you're in it to visualize it and believe it.

All eggs in one basket or portfolio approach?

Kenny: There’s also the portfolio approach of side hustles where you try many things and see what sticks. There's obviously a limit to that because if you start to expand a lot and start doing a few things here and there, you don't really get that compounding effect. Because if you do so many things at the same time but you don't move past a certain threshold, then you won't get that compounding effect. What do you think about this whole portfolio approach?

Jamie: It goes with the personality type. If you're the type of person who can't really stick to one thing and you need multiple things, then I think you need to embrace that. But you need to be realistic about it. I have 11 income streams. There's no doubt in my mind that if I picked one of them and focused all my time on that one, it would be bigger and maybe bigger than all 11. But the thing is that with 1, I may get bored with it. With 2, I don't have the safety of the numbers, and 3, there's no guarantee that it would work. I'm very much in favour of the portfolio, but as you said, you have to be realistic. You have to know that if you’re going to divide your attention into 4 different projects, then they're going to grow at least 4 times slower, maybe even more than if I picked one and ran with it.

I'll often tell people who have 2-3 ideas that they have to choose. They could go two ways, and there's not one that's better than the other. Some people will say, “Oh, you need to focus everything on one.” That's fine. If you want to do that, go and focus on one and see what happens. But if you want to launch 3 projects simultaneously, go ahead. It's never been easier and simpler. But you have to be realistic. You have to say to yourself, “I only have 30 hours a week that I could give on the side. I'm going to give 10 hours to each, or I'm going to give 20 hours to one and 5 hours to the other two.” Break it up however you feel, but know that when you're taking hours away from one, you're not putting all the compounding into your favour. That's essentially what I did. When I started, it was all about what I call digital assets. So, I would build or create designs for print on demand. I created printables for Etsy, I created books for KDP. I didn't tie them to any brand. I didn't do any promotion. All I did was leverage the different marketplaces that I could for sales. It worked great.

But I made the decision in February of 2022 to launch a newsletter. As soon as I started writing the newsletter, I fell in love with the whole concept of newsletters. After a month or two, I barely built another digital asset. But they're still generating income nonstop. It's not huge amounts of income, but it's still income. That time wasn't lost because they were all independent of each other. I didn't need to promote them, and they just generated sales. At the time, my thinking before the newsletter was, “I will just keep building up my portfolio of assets, and the income will come with it.”

While that's true, by next year, my newsletter will make more money than Amazon KDP and probably even all of my assets together. If not, next year, for sure, the year after. It's made me pivot my approach to what I do, but also what I suggest other people do.

There's a middle ground between having your own audience and building digital assets in your free time. If they don’t make money, you could offer them to your audience. If you are very introverted and you don't want an audience, well, you could do it without the audience, too.

Kenny: Putting all your eggs is obviously a huge risk, but on the complete opposite, if you have a lot going on, you risk being dispersed. You need to understand the pros and cons of each approach when you choose one. As you said, where you put yourself on that scale is based on your personality, risk tolerance as well and your curiosity.

Jamie: And how much time you have. There are a lot of different factors. You may have one bigger egg in your basket, but maybe there's nothing inside the egg. Maybe it's going to break. Whereas, if you have 15 eggs in your basket, they'll be smaller. But maybe one or two breaks, who cares? Especially if you're building on “rented land.” I'm very pro building on rented land, but it goes hand in hand with the many eggs basket.

If I went all in and focused only on Amazon KDP, and they shut down or they closed my account, or they made some sort of change in their algorithm, that will directly affect my income, and I'll be done, I'll have nothing. Whereas the more diverse you are, the more different places you're building on. If one goes under, it's very unlikely that six of them will go under at the same time. But if one goes under, it's not that big of a deal. That's what I love about digital assets is that you can build them. If you have 3 hours this week, you could build one. If you only have 15 minutes next week, you could build one. You have 6 hours the week after, you could build many.

Once you've built it and you've put it in these marketplaces, if you want, try and promote them, and you'll definitely get more sales. You could not promote and keep building, you'll get organic sales, especially on Amazon. As long as you're doing something that's worthwhile and quality, you'll get organic sales.

Promotion vs relationship-building

Kenny: I love SEO and getting inbound leads. It’s just the best. Because you just build it once and invest some time in it, and then reap the rewards of that without having to promote your stuff constantly. Not like social media where you have to constantly create content.

Jamie: Exactly. I try not to promote my stuff. I've created so many assets. This is not even just paid products. I've created maybe 20 different free templates, guides, checklists, and challenges. From time to time, I'll promote them in my newsletter because I'm running late and I don't know what to put in or I didn't create any new content, so I'll promote one. The other day, I promoted a 30-day free engagement challenge, and I had 100 people sign up. So many people told me, “Whoa, this is amazing.” I created this 3-4 months ago and didn't promote it. That's what I like about what I do, is that my newsletter is not about funneling people to buy stuff.

”Here are things that I think could help you. If you want, I have all this stuff too that you could buy to help you get where you need. If you don't want to buy, then you don't. I'm okay with you just coming along for the content.” The best type of person in my audience is not the person who buys the most. It's not the person that's been there the longest. It's the person that replies the most. There are people I have conversations with who have never bought anything, but we have awesome conversations about side hustles and assets. That's the most fun of having a newsletter, which is weird because I'm an introvert. If you had gone back to when I started Minimalist Hustler and told me about the newsletter, I'd say you're crazy.

It just turns out I won't even do video calls. Even when I started the newsletter, people would ask for video calls. I always said, “No, I'm not doing that. No calls. I don't do calls.” I turned so many people away until I realized that the problem with calls was never the actual format of the video call. The topic was always the problem. My experience with video calls was only my full-time. But now work meets passion, so it's much more enjoyable all around.

Kenny: You're not focused on selling products but mostly on building relationships with people. That's a totally different focus. So when you hang out with people, you're not trying to sell them stuff all the time. Whenever the occasion arises, then you say, “Hey, by the way, I think this stuff would help you.”

Jamie: The other day, we went to free skate at the arena at the rink. One of the parents there, watching her kid as well, turned to me and asked, “What do you do?” I explained to her what I did, and she's like, “Oh, my husband's looking into this. I'm going to buy one of your ebooks.” No, you're not going to buy my ebook. I'll give it to you if you want, but you won't buy it. I'm so anti-selling that if I feel like I've sold somebody on something, I'm cancelling it right now. You just take it, don't worry about it.

For the longest time, I would give away my main ebook for free to anybody who signed up for my newsletter. “Thank you, take it.” I've given thousands of copies away for free. Now somebody convinced me to put a thank you page where I offer my book at 50% off. I get 2 to 4 sales a day. I could have made $21,000 in profit in the past, but it's built so many relationships, and I just love getting up in the morning and seeing people reply to my newsletter and ask me questions.

Kenny: It's way more valuable than just that profit that you lost. Now, you’re still making a bit of profit on it.

Jamie: Oh, for sure. That's the whole name of the game. But the thing is that if you don't focus on it, I mean, you still have to think about it because you still have to figure out how you're going to pay the bills. But if you don't focus on it usually comes with the value that you provide, as long as you are providing value.

What inspired you in Jamie’s story? Share a comment below.