How I Built A $420K/Year Content Business Helping People Make Extra Money
Hello! Who are you and what business did you start?
In 2013, I started the Side Hustle Nation blog, accompanied by the Side Hustle Show podcast. Naturally, it was a side hustle for me. There was no business model or business plan in the beginning — I just set out to create the kind of content I wanted to consume: light on the theory, heavy on the tactics. With a $50 mic in the corner of the living room, I started interviewing other side hustlers and entrepreneurs about how they got their ideas and grew their businesses.
Since then, the podcast has been downloaded over 23 million times, and the website reaches millions of visitors a year. Turns out, I wasn’t the only one curious about realistic ways to make extra money!
When I launched Side Hustle Nation, I didn’t have an “audience” to speak of. I had an email list of 11 people -— entirely made up of friends and family. But what I did have (and what you have as well) is a personal and business network going back several years.
What's your backstory and how did you come up with the idea?
What qualified me to talk about side hustles in the first place? Well, a separate side project had been my ticket out of Corporate America. That project was a comparison shopping site for shoes that did $20-30k a month at its peak. After 3 years of plugging away at it nights and weekends, I finally got up the confidence to give my 2-weeks notice at work. When I quit my job at 25, I thought I was the smartest person in the world — I’d found a way out of the rat race. I’d beaten the system!
Like every business, my shoe site had lots of ups and downs, which led me to create several other online side hustles over the next few years. For the sake of disclosure, most of those died a quiet death in some lonely corner of the Internet. But a couple had some staying power. The first was a directory and review platform for virtual assistant companies called Virtual Assistant Assistant. I started that in 2011, and sold it in 2020. (In total, it ended up being a $550k project, including the proceeds from the sale.)
The other project that stuck around was Side Hustle Nation. I’d been blogging for years just on my personal domain and found I enjoyed content creation — even if no one ever read my posts. Because of that, I thought of myself as a writer first, and the podcast was almost an afterthought. That’s why I was surprised when the podcast grew quite a bit faster than the new Side Hustle Nation blog did in the first year. Something about the approachable, curious, tactical side hustle focus resonated with listeners. (And timing helped too! Even though it felt crowded at the time, 2013 was the early days for both podcasting and the “side hustle” movement.)
I reasoned I had some level of credibility in having built a side hustle to the point I was able to quit my job, but more than my expertise, the show relied on the stories, ideas, and tactics of the guests.
Take us through the process of designing, prototyping, and manufacturing your first product.
Because the site was a side hustle, it didn’t need to earn revenue right away. And when you’re giving away a free podcast and free blog content, that’s probably a good thing!
The first thing I sold through the site was a private mastermind group. It was a suggestion from a friend of mine, Alex Barker. He said, “You’ve got people paying attention to you; they’d probably pay to hang out with you, too.” This was 7-8 months into writing the blog and hosting the podcast, and I probably had around 700 people on the email list at that time. I created the 3-month Side Hustle Nation Inner Circle mastermind, priced at $99/mo. In the end, I got 6-7 applications and ended up running the groups for the next couple of years. They were a lot of fun and many of the participants are still active in a variety of businesses.
Since then, I’ve added affiliate relationships, brand sponsorships, and my products and services to the revenue mix.
The original 2013 homepage:
Describe the process of launching the business.
When I launched Side Hustle Nation, I didn’t have an “audience” to speak of. I had an email list of 11 people -— entirely made up of friends and family. But what I did have (and what you have as well) is a personal and business network going back several years. So what I did was open up a new Gmail compose window and started going through the alphabet.
I’d type “a” and it would auto-fill with my friend Aaron. Hey, I haven’t been in touch with Aaron for a while. I’m curious about what he’s up to. Plus, it’s a chance to share my latest project. I invited Aaron and lots of other contacts to download my new podcast.
Hundreds of warm-ish emails later, The Side Hustle Show was getting 10s of downloads a day. It wasn’t much, but it was fun to produce and was seeing just enough traction to keep going. And I’m glad I did! Here’s what the first 4 years of the show look like in terms of download growth:
I also did a bit of guest blogging and, in general,l tried to embed myself in the communities of entrepreneurs I was trying to reach. And it didn’t feel like work because I was one of them myself!
I often ask myself why this business worked when so many similar blogs and podcasts didn’t. I think the answer lies in persistence and paying attention. Those two things combined have been the difference between thriving and dying on the vine.
Since launch, what has worked to attract and retain customers?
A big inflection point came in mid-2014 when I finally realized that the podcast was not a business in itself, but rather a content marketing arm for a business. (Since then, the show has become a viable standalone business on the back of sponsorships, but it wasn’t then.) Treating it like content marketing led me to be far more proactive about turning anonymous listeners into email subscribers.
What worked for me was creating episode-specific lead magnets, and inviting listeners to download those in exchange for their email. These were essentially full-text summaries of the episodes, but because of the detailed and tactical nature of the show, they performed well. Within 3 months, I went from 1,000 subscribers to 3,000. Within 6 months, it was 6,000, and within 12 months it was 12,000 subscribers -— a huge turning point.
All of a sudden, I had a sizeable email audience I could promote each episode too, and they had something in their inbox they could easily forward to a friend who might be interested in the topic. You can see it in the download chart, that’s when things start to climb a little faster. On top of that, the relationship with these subscribers was really strong since most came after spending 30-40 minutes with me and my guests in their earbuds week after week.
Today, Side Hustle Nation is about to cross 100,000 email subscribers. Each week, I get to practice the fine art of email subject line writing and come up with a compelling hook for the episode.
To grow the audience, I think about “Climbing the Listener Pyramid”: a 4-step journey from Strangers to Listeners to Subscribers to Fans. Every piece of content I create is designed to ascend people on that journey. (I even created a full course on growing a podcast.)
In 2015, I added a Facebook community, which is now over 50,000 members strong. It’s a way for side hustlers to ask and answer questions, and support each other in their mission to build extra income streams.
Another important turning point for the business was learning and leaning into SEO and affiliate marketing. Even though the blog was generating some traffic from Google, it was almost accidental -— I didn’t pay any attention to keyword research or really what action I wanted visitors to take after they landed on the site.
That changed following FinCon in 2017 when I realized that some of the most valuable sites in the personal finance space earned money directing organic traffic to relevant affiliate offers. But in addition to that, my strategy is to try and take that cold Google traffic and convert readers into podcast listeners to strengthen the relationship over time. That’s why you see a lot of the content on Side Hustle Nation that ranks well in Google, like this post on side hustle ideas, which intentionally references relevant podcast episodes.
How are you doing today and what does the future look like?
My focus today is on creating great podcast content and great written content. The business runs pretty leanly so an ongoing focus of mine is creating systems and processes to remove me from certain aspects of the operation.
It’s super rewarding to hear from members of the community that they’ve taken ideas and tactics from the content and applied them in their businesses. In that way, the content is almost self-perpetuating -— I find that most of the best episodes come from within the community rather than some outside pitch.
I don’t have any specific revenue goals I’m targeting, but instead, focus on shorter-term experiments and projects. For example:
- we’re playing around with short-form video for the first time
- we added newsletter sponsorships as a new revenue stream this year
- I’m working on a “find your side hustle” quiz to help people narrow down their options
I’m super grateful to be able to do this work and get paid for it.
You don’t have to reinvent the wheel or come up with something no one’s ever seen before. Focus on solving real problems and see what kind of traction you can get.
Through starting the business, have you learned anything particularly helpful or advantageous?
I often ask myself why this business worked when so many similar blogs and podcasts didn’t. I think the answer lies in persistence and paying attention. Those two things combined -— though I’m sometimes pretty slow on the uptake -— have been the difference between thriving and dying on the vine.
First, not many of the podcasts that started around the same time are still actively publishing. It’s been 9.5 years and over 500 episodes! It feels like a habit at this point, and hopefully, it feels like a consistent part of the listeners’ weeks as well. They know there’s going to be something new every Thursday, and hopefully, they find it compelling and helpful. But it was years before the podcast started to generate enough revenue to be considered a full-time income.
Second, I think paying attention to what’s working for other businesses is a hugely underrated entrepreneurial skill. For me, that meant noticing how other podcasts, websites, and newsletters are monetizing. It’s meant intentionally creating content around targeted topics and keywords, rather than just whatever popped into my head. That meant listening to my audience and their biggest struggles and creating content and products to answer those.
What platform/tools do you use for your business?
I keep a fairly-updated list of my top online business tools and resources here, but here are the main ones that come to mind:
- WordPress
- ActiveCampaign - for email marketing and automation
- LeadPages - for email capture and quick landing pages
- Teachable - to host online courses
- Zencastr - to record remote interviews
- Affluent.io - for aggregate affiliate reporting
- Ahrefs / Ubersuggest - keyword research
- Otter.ai - to transcribe podcast recordings
- Podcast Fast Track - the editing service I’ve used for years
- Descript - a cool tool to edit videos by editing the transcript
- Screencast-o-Matic - screen share videos, light video editing, creating workflow documentation
- Lastpass - to securely share login information with team members
- Canva - for thumbnails and other graphics
What have been the most influential books, podcasts, or other resources?
In college, my roommate made me read Rich Dad, Poor Dad, which helped solidify a lot of ideas that were already in my head. The big takeaway: when income from assets you control exceeds your monthly expenses, you’re free.
In the early years of Side Hustle Nation, I drew huge inspiration from Pat Flynn’s Smart Passive Income.
Finally, I owe a ton to attending online business conferences in real life. My favorite is FinCon, an annual event for personal finance content creators, which I’ve been attending since 2015. Being able to connect with and collaborate with other entrepreneurs has been super valuable.
Advice for other entrepreneurs who want to get started or are just starting out?
Don’t wait for the perfect business idea to take action on. Every successful business I had was a version of something that already existed. From painting houses in college to comparing prices on shoes to interviewing entrepreneurs -— it had all been done before. I just served a slightly different audience or did it in a slightly different way. And sometimes that’s all it takes. You don’t have to reinvent the wheel or come up with something no one’s ever seen before. Focus on solving real problems and see what kind of traction you can get.
The second thing is to position each new project as an experiment in your mind. That permits you to test things out and forgiveness if and when things inevitably don’t go as planned. Failure still stings, but I find I’m less upset about it if I thought of it as an experiment from the start.
Where can we go to learn more?
- Side Hustle Nation
- Add The Side Hustle Show to Your Podcast App
- My big list of side hustle ideas
- The Side Hustle Nation Facebook Group
If you have any questions or comments, drop a comment below!
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Download the report and join our email newsletter packed with business ideas and money-making opportunities, backed by real-life case studies.
Download the report and join our email newsletter packed with business ideas and money-making opportunities, backed by real-life case studies.
Download the report and join our email newsletter packed with business ideas and money-making opportunities, backed by real-life case studies.
Download the report and join our email newsletter packed with business ideas and money-making opportunities, backed by real-life case studies.
Download the report and join our email newsletter packed with business ideas and money-making opportunities, backed by real-life case studies.
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