Nick Loper

Chief Side Hustler at

Nick Loper helps people earn money outside of their day job. He’s an author, online entrepreneur, and host of the award winning Side Hustle Show podcast, which features new part-time business ideas each week.

As Chief Side Hustler at, he loves deconstructing the tactics and strategies behind building extra income streams.

At home, Nick is a husband and father to two active boys, ages 2 and 4. Together, they enjoy riding bikes and exploring their hometown of Livermore, California.

Where did the idea for come from?

It came from a combination of factors. I wanted to start a more personally-branded project and found the topic of side hustles and creative ways to make extra money fascinating. In 2008, my side hustle had been my escape path from Corporate America, so I was excited to spread the gospel of this lower-risk brand of entrepreneurship.
Because I’d already been blogging for a few years, I thought of myself as a writer. I started The Side Hustle Show podcast almost out of peer pressure (hey, podcasting is the next big thing — everybody’s doing it!), and I was surprised that the show gained traction much faster than the blog side of things.

What does your typical day look like and how do you make it productive?

If I can get up before the kids (2 boys, ages 2 and 4) and get a workout in first thing in the morning, my day is off to a great start.

I normally work 8-5, Monday through Thursday, and try to theme my days as follows:
Mondays: Content production – preparing podcast episodes, writing blog content, or editing content from freelancers.
Tuesdays: Meetings days. This is the day I record with guests for The Side Hustle Show and am interviewed on other shows.

Wednesdays: Wednesdays are usually a lighter day. I tend to focus on some of my own personal side hustles in the morning and have the afternoon reserved for any necessary administrative tasks.

Thursdays: Thursdays are earmarked for Side Hustle Nation growth projects. In the past, this has meant writing books, building courses, working on new marketing initiatives, SEO experiments, and other stuff like that. A couple of my current projects are improving the speed of the site and re-thinking some of my email marketing strategies.

Fridays I’m off with my boys.

How do you bring ideas to life?

Experimentation and practice. You never know if something is going to be successful until you put it out there.
It took years of podcasting before I considered myself “a podcaster.” You have to start before you’re a pro, which is hard for Type-A / perfectionist personality types! But remember, every All-Star was once a rookie.

What’s one trend that excites you?

I don’t know if this counts, but the $200-250 a month I’m making on YouTube right now is the income I’m most excited about. I suck at video but it’s a totally new frontier for me, much like podcasting was in 2013.

What is one habit of yours that makes you more productive as an entrepreneur?

I list out my top 3 priorities for the next day the night before, so I know exactly what to tackle — and in what order — when I start work. I try to force myself to knock out at least the first item before diving into “reactive” mode by checking email or social media.

What advice would you give your younger self?

Just because something’s already been done, doesn’t mean you can’t do it too. When I started The Side Hustle Show, there were already dozens of “entrepreneur interview” podcasts. Did the world really need another?
“If you can’t be first, be different,” was the advice Jonathan Mendonsa from ChooseFI gave me years later. Everyone will bring their own unique spin to the topic, and the pie is big enough for more than one player.
Early on, I’d think of these awesome ideas for blog posts, only to the google the topic and find someone had already written about the same thing. Well, have you ever gone to Google and gotten zero results? Of course it’s been done before, but that shouldn’t necessarily dissuade you from trying to build something better.

Tell us something that’s true that almost nobody agrees with you on.

Interviewing famous guests on your podcast won’t make it a hit. Every new podcaster wants to get “big name” guests because they think that’s the ticket to grow their show.
“If I could just get Garyvee, and somehow get a small percentage of his followers to follow me, I’ll be off to the races!” The thing is, you probably suck at interviewing when you’re first starting out, so you’ll have an awkward conversation at best. Then, this famous guest of yours isn’t going to share it with their audience because it’s not a good share for them. Their audience already knows their story!
Instead, focus on helping your audience take the next step.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

The process looks something like this:
Start an experiment, understanding that it might fail.
If it works, do more of that.

What is one strategy that has helped you grow your business?

A big turning point for me was recognizing that a podcast — at least at the numbers I had a year into the show — is not a business. Instead, it’s a marketing channel for a business.
So what I started to do (and went on to do this for years) was create episode-specific lead magnets. I called them my “highlight reels” and they were essentially PDF summaries of the episodes with all the guests’ top tips. Once I started inviting listeners to download these highlight reel files, my email list went 6x’d in the next 6 months.
Now I had a much larger group of subscribers I could communicate with on a regular basis, promoting blog content, the latest episodes, and the occasional affiliate offer.

What is one failure you had as an entrepreneur, and how did you overcome it?

I was painting houses in college, and I remember one customer wanted a bright red front door. The painter I hired had some experience, but this door was a disaster. There was no denying it, and it was super-obvious right at the front of the house. Despite our best efforts, we couldn’t make it look right.
I ended up having to go buy a completely new door and hire another exterior painting company to complete the job I was hired to do. It was super embarrassing — and expensive — but was an important lesson about biting off more than I could chew!

What is one business idea that you’re willing to give away to our readers?

One idea I think would be cool would be a used car concierge. Car shopping is a huge pain, takes a ton of time, and is a big-dollar decision. What if I could hand over my criteria to an expert car shopping specialist / negotiator. This person could find all the vehicles in my area that match, present my best options, pre-negotiate the best deal, and then all I have to do is show up to inspect, test drive, and sign the paperwork.
They could charge a flat fee or maybe even a percentage of the sale.

What is the best $100 you recently spent? What and why?

Last year I ordered a podcast mic ($70ish) I could loan out to guests who don’t have their own audio setup. I know it makes them feel awesome when it arrives in the mail, and I know it makes the show sound better for listeners.
And this month I spent $12 mailing books to members of the Side Hustle Nation community. That kind of stuff makes me feel great and doesn’t cost a whole lot either.

What is one piece of software or a web service that helps you be productive?

LastPass for sure. This little browser plugin generates secure passwords for every new site I need one, remembers all my old ones, can automatically log me into websites, and securely share passwords with team members. Hands down this is the tool I use the most on a daily basis, and I’ve come to totally take it for granted. Even if it just saves a couple seconds each time, the amount of joy it gives me in not having to remember and type in the login information is huge. And there’s a really robust free version!

The other tool, if I’m allowed another, is TextExpander. This will allow you to create your own keyboard shortcuts for the phrases, websites, emails, directions, etc. that you type most often. I have dozens of these set up and use them throughout the day. A free alternative is a Chrome extension called Auto Text Expander.

What is the one book that you recommend our community should read and why?

The Go-Giver by Bob Burg is a great little parable about the power of giving first. It solidified a mindset shift for me, from “how can I make money?” to “how can I help people?” Because once you’re genuinely helping people, the money tends to naturally follow, and that’s exactly what I found. First by accident, and later on purpose.

What is your favorite quote?

“If we weren’t all crazy, we would go insane.” –Jimmy Buffett

Key Learnings:

  • Look at new projects as experiments. This lessens the sting of the inevitable failures that come along the way!
  • Look at where you’re getting the best results, and double down.
  • Identify your top priorities each day, do those consistently, and you’ll see meaningful progress.