Nick Loper: Side Hustle Nation Creator Case Study

Nick Loper - Side Hustle Nation - Interview

Please tell us about your business?

I started the Side Hustle Nation website and accompanying podcast, The Side Hustle Show, in 2013. I thought of myself as a writer first, so it was surprising when the podcast started to get traction faster. (And by “traction”, I mean just enough listenership to motivate me to keep going.)

With the podcast, I set out to create the show I wanted to listen to: light on the theory, and heavy on the tactics. I wanted people to finish the episode and be ready to take action. By interviewing successful side hustlers to deconstruct their marketing methods, tools and resources, and growth steps, slowly but surely the show started to gain a loyal following.

Today, the podcast reaches around 100,000 listeners a month and has been downloaded over 25M times in total. It’s all pretty crazy to think about, since it started as just a little side project experiment with a $60 mic in the corner of the living room.

How do you make money?

Today, the primary revenue drivers of the business are sponsorships on the podcast and affiliate relationships through the blog and email list.

I also sell a handful of digital workbooks, self-published books on Amazon, and my own online courses.

All told, it’s a comfortable multi-6-figure business I get to run from home.

What works to grow your audience?

The initial audience was almost entirely from the podcast. There are lots of podcast growth strategies out there, but two are the most important.

First, guest on other relevant shows. The biggest spikes in exposure I’ve seen have come following an appearance on other shows in the entrepreneurship and personal finance space.

Second, with every episode you create, think about climbing the listener pyramid.

Listener Pyramid

Think, how will this episode help turn:

  • Strangers into listeners?
  • Listeners into subscribers?
  • Subscribers into fans?

If you can do that well — on top of having compelling content — word of mouth will start to spin in your favor.

The other challenge is that podcasting is a very anonymous medium. You can build a really strong relationship with listeners, but don’t get much information on them. That’s why I make an effort to convert listeners into email subscribers with a variety of lead magnets and content upgrades.

My latest effort on that front is a “personalized playlist” quiz, that drove over 600 new email sign-ups last month.

The other big driver is SEO to the website. It ranks well for a variety of side hustle-related keywords, reaching over 200,000 unique visitors a month. My goal is to translate those visits into:

  • Podcast listeners
  • Email subscribers
  • Affiliate conversions

What has been your most popular content?

Most of my best-performing content has been born from my own curiosity. One of the very first posts I published was this big list of side hustle ideas. It’s been a “pillar post” for almost 10 years now and has been viewed over 3.2M times.

Similarly, this list of ways to make extra money started as a much longer post, detailing as many different ways as I could find. (As it ballooned to over 11,000 words, I pared it down for the sake of readability and SEO.) The original post did so well, it actually gave me the inspiration to expand on it and create a whole book, called Buy Buttons.

This post on paid market research studies is another great example. It’s closing in on 1M lifetime pageviews, and it all started when I got invited to a paid focus group in San Francisco. I was excited by how easy and fun it was — and riding BART on the way back, I started looking for other companies that might pay you for your opinion.

On the podcast side, episodes on online business and affiliate marketing are usually hits, but a format that’s consistently super popular is my annual roundup of 10 Creative Side Hustles. I’ve aired a different version of this on Thanksgiving for the last 5 years, and they always do really well. Over the years, it’s included side hustles like renting out backyard chickens, getting paid to wait in line, going after robocallers, the 7-figure lemonade stand, and lots more.

Have you had any major inflection points on your creator journey?

There are a few that come to mind.

The first was in 2014, a little over a year into the project. It was still very much a side hustle to the main business I was running at the time, but was a lot more fun to work on.

At that point, I (finally) realized that the podcast wasn’t a business in itself, but was instead a content marketing channel for a business. When I started treating it as such -— by creating episode-specific lead magnets -— the email list growth really started to take off. At that time I had around 1000 email subscribers. Within 3 months of implementing this new strategy it was 3,000; within 6 months, 6,000. And it was off to the races from there.

Another big spike came after guesting on Entrepreneurs on Fire in 2015. John had a huge listenership, and we got a chance to talk about The Side Hustle Show, which had just been nominated “Best Business Podcast”. That nomination gave some credibility to a much smaller show that much of John’s audience would still find benefit in.

And finally, in early 2017, NY Times bestselling author Chris Guillebeau launched a very similar-sounding podcast called Side Hustle School. At first, I thought I was toast. “Hey, this is my territory!”

But I never saw a bigger spike in downloads than I did that first month of his show. He brought a lot of new listeners into the fold and introduced a lot of new people to the concept of “side hustling.” And when they searched for more information on it, who did they find? Me.

It was proof that a rising tide lifts all boats.

How did you get started?

I chose this niche based on some soul searching, like:

  • What do you never get tired of talking about?
  • What do you have experience in?
  • What do other people ask you questions about?
  • What do you want to be known for when someone Googles you?

The topics of side hustles, online business, and creative ways to make extra money were (and still are) super exciting to me. I thought I had a decent grasp on them after having quit my job to pursue my original side hustle full-time, but I’ve learned so much more over the years of talking to hundreds of other entrepreneurs.

To get initial traction for the project, I just started with my existing network. It wasn’t huge and I didn’t have any pre-existing audience, but I just went through Gmail and started emailing everyone I could think of (I literally would type a letter in the address bar and see email what auto-populated). I let them know I launched this new podcast and that it would help me if they could go download a few episodes.

But beyond tapping into my own network, it was more about carving out some mindshare that Nick was now the side hustle resource. If anyone they knew was interested in the topic, I wanted to be top of mind.

How much content do you produce each week or month?

The Side Hustle Show comes out every Thursday, rain or shine.

I’d love to produce more written content, but do spend quite a bit of time maintaining the archives vs. creating completely new posts. Still, there’s a lot of articles on the “to do” list!

How many hours per week do you spend on the business now?

It varies, but 25-30 hours is probably a good average. That includes:

  • Vetting guests and outlining episodes
  • Reviewing transcripts and prepping for editing
  • Interfacing with advertisers and affiliates
  • Optimizing existing blog content
  • Creating new blog content
  • Creating video content

I don’t spend much time on social media, which is definitely an opportunity for growth.

Do you have any employees or assistants?

I have a pretty lean team of on-demand specialist contractors. Here’s what my current team looks like:

  • Dedicated administrative VA – email triage, customer support, podcast spot checking, and lots of other stuff. Usually 5 hrs a week, but could be more.
  • Podcast editing service –
  • General VA – – Weekly repetitive tasks and ad hoc assignments.
  • Video Production VA – 5-10 hrs a week. She creates short-form video clips from the podcast episodes and uploads them to TikTok and YouTube. She also creates full-episode videos for YouTube.
  • Show Notes Writer – – Summarizes each episode and creates the text version for the website.
  • Bookkeeper –
  • Website Support –

What are the key apps, software or tools you use in your business?

  • WordPress
  • TextExpander
  • Beaver Builder
  • GeneratePress
  • LeadPages
  • ActiveCampaign
  • Descript
  • Screencast-o-Matic
  • Awesome Screenshot
  • Zencastr
  • GroupLeads
  • TryInteract
  • LastPass
  • Ahrefs
  • TubeBuddy
  • Google Docs

Those are the big ones off the top of my head!

If you were starting over today, what would you do differently?

I definitely think I could accelerate the journey if I had to start over.

I would have paid more attention to audio quality at the beginning … some of the early episodes sound a bit rough! I would have figured out the email opt-in thing earlier, since that was such a huge turning point for the business.

In a way, I’m happy with how the early days of the blog were more personal-journey type of posts, but they certainly didn’t attract evergreen readership. It would have been beneficial to focus more on SEO early on … it was probably 3-4 years before I looked up from my desk and took notice of what other sites in my niche were doing!

But all in all, super grateful to have started this thing. It’s truly been life-changing, and I’ve met some incredible friends and entrepreneurs along the way.