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054: Turning Your Side Hustle into a Full-time Business (w/ Nick Loper)

Nick Loper is an author and online entrepreneur featured on The New York Times, Forbes, Fortune, and speaking at a TEDx event. His latest role is as Chief Side Hustler at Side Hustle Nation, a growing community of aspiring and part-time entrepreneurs, where he also hosts the top-rated Side Hustle Show podcast. 

He is the author of 4 books including Work Smarter: 350+ Online Resources Today’s Top Entrepreneurs Use To Increase Productivity and Achieve Their Goals, which became an Amazon bestseller in 2014. Nick has been working with virtual staff since 2005 and has a free course on how to hire a high quality and long-term virtual assistant. He also runs the web’s leading virtual assistant company directory and review platform, Virtual Assistant, with more than 100 VA companies and 700 user reviews. He has helped thousands of readers identify their outsourcing opportunities and take action. 

Period in full-time business 

Nick has been self-employed full-time since 2008 and worked in business as a side hustle since 2004. 

Core revenue streams 

His biggest revenue streams on his podcast, The Side Hustle Nation, include sponsorships and affiliate revenue. He also has several other affiliate websites that do well. He was able to leave formal employment because of an affiliate website. It was a footwear comparison shopping site built on an affiliate model and used to refer traffic to Amazon and Zappos, and Nick would earn commissions from the resultant sales. 

He does self-publishing with books on Amazon including some on side hustling. He also does some freelancing work which including book editing for other non-fiction authors, sales courses on Udemy, and selling products on Fiverr. 

Key focus going forward 

The podcast has been his main focus in the last year. It started out as an afterthought experiment but it has grown faster his blog to become his main focus. 

Reason for podcast growth 

Nick thinks the main reason the podcast has grown so fast is because of word of mouth marketing but he also highlights podcast marketing and iTunes optimization as some of the other reasons. Some episodes have had people engaged and talking about the podcast. 

Focusing on his niche 

Nick says that focusing on the side hustle side of business may have contributed to the podcast’s success. He only had an email list of 11 people to market the podcast to when he was starting the podcast and that’s how he built his audience slowly. 

Leaving corporate 

The footwear comparison shopping site was the business that helped him leave his job. He used to intern at a shoe retailing company in Seattle which had a brick and mortar store but decided to try selling the shoes online. The online segment of the business grew 10 times faster than their brick and mortar shop. That’s how Nick got exposed to affiliate marketing, pay per click advertising and SEO (Search Engine Optimization) which enabled him to build his own footwear comparison shopping site. 

When he was running the site, he was very reserved and heads down working on it. He didn’t mingle with any people in the business world and faced a lot of challenges with the business. At one time he had a problem with Google and it was very frustrating because 80% of is traffic was coming from Google ads. Later the problem was sorted but it taught Nick the importance of diversifying his business. Later on he started several other different side hustles, most of them flopped but a couple have stayed afloat including the Side Hustle Nation site. 

Knowing when to leave corporate 

One of the factors that helped him leave his formal job included the income he was making from the site. It was not replacing his salary in the beginning but he felt that if he could work solely on the site, that it could make him more money. 

Getting the first sponsors 

He says the first sponsors reached out to him about a year ago and asked him to consider doing an ad on the show. To achieve that, he started by self-sponsoring his own products and services or did affiliate ads for companies that he liked including AirBnB. That sent a signal that his podcast had sponsors and therefore made it easier to get serious sponsors when needed to. 

Today, he uses a service called AdvertiseCast which enables him to put up the show and get advertisers who buy spots on the show. Nick just did a couple of deals with some companies. 

Growth strategy now 

Right now Nick has been working on building the podcast’s audience by building on its discoverability on iTunes and social media while also doing SEO. He has also been working on turning listeners into subscribers by for example giving them valuable content. He does content upgrades which comprise of episode specific opt-in offers which have raised his email list to more than 6,000. He also provides a highlight reel of each episode and includes that in his newsletters. 

He recently built up 8 to 10 different welcome sequences based what a person opted in for which ensures that they get a welcome/on-boarding sequence that meets their specific preference. Initially, every person got the same generic autoresponder sequence and it was not working very well in engaging or serving the audience. He has gotten more replies from those messages. Nick has not monetized them yet but there are some links on the sequences to posts on the podcast site that are monetized but it’s not well orchestrated. That is mainly because he currently doesn’t have any flagship course. 

The first way Nick monetized the podcast was with a private mastermind but it has been on hold for a while. He has been trying to come up with a way to restructure the mastermind so that it can more impactful for participants. 


Nick has tested doing other products apart from the podcast. An example is what he is doing with the opt-in offers. He also does a few joint ventures every year like webinars and they do very well. 

Affiliate marketing for bloggers and online marketers 

Nick says affiliate marketing is one of the best ways to get started because one doesn’t have to create any products. It’s always better especially when one is recommending products or services that they use and trust. He recently did a post on the redesign of his website and he shared an affiliate link to the IT service that he used to do the redesign. 

He did very well in affiliate marketing Udemy courses through blog posts. He kick started that with an email to his list and also reached out to all the instructors that he featured, and they were very supportive in sharing it to their social media channels. That way, it ended up ranking well on Google. 

Tip 1: Always try to work in the products or services you are recommending into all the content on your site. 

Tip 2: You can still provide helpful content and make money from it too 

Generating revenue from affiliate marketing 

His post on Udemy courses has generated over $30,000 within a year and a half. It generated $6,000+ in the first month and then sustainably kept generating fairly good revenues in 2016. In 2017, Nick updated it with the latest offers and relaunched it in January. That month it made around $12,000 and has been doing well so far. 

Fear of failure and the worst moment with Side Hustle 

Nick didn’t take the leap of leaving his formal job until he had built some track record with his business. He says he is very risk averse and likes to start projects on a small scale. The podcast was a very big step out of his comfort zone. He also did a TedX Talk a few years ago and it was the hardest thing for him to rehearse. 

Shutting down the mastermind has been the worst thing for Nick in the last 12 months. A few years ago he did a 30-day side hustle challenge and the feedback he got from participants was positive but people were not seeing results from it within the 30 days and Nick has to redo it all over again. 

Tip: Fear of failure can be paralysing but you have to look at what the worst case scenario is, so you can make small improvements or make it so that the worst case scenario is not that bad. It’s probably not life threatening, you can always get a job if it doesn’t work 

Faith, Fun, Family, Finances, and Friendships 

Family comes first, fun and friendships fall into the same group then finances and faith. 

A day in life when starting out Side Hustle Vs a day in life now 

Tuesdays are meeting days for Nick and earlier in 2017 he started a theme day project where Tuesday is bust doing recordings, calls, and different meetings from 8 to 5. He sets aside Monday as content creation day for Side Hustle Nation including shows. He is trying to get to a point where he can be editing shows for 3 or 4 weeks out.  

Wednesdays are when he works on the other Side Hustle projects that he has like websites including the administrative tasks involved with them. He dedicates Thursdays to mastermind calls in the morning and then does the weekly newsletter while the rest of the day is set aside for growth projects like the recent email migration and website redesign. He starts the day on his treadmill desk. 

Email system switch 

Nick switched from Aweber to ActiveCampaign and even though he is still learning how to use it, one the most important features for him was the geo-tagging features that are based on a person’s IP address and uses it to estimate where they are in the world. He can use that to host meet ups all across the country and even meet with people all over the world like they did in Japan in 2016 where they had 5+ people attend his meetup. 

Tool and Resources 

  1. AdvertiseCast – Podcast Advertising Network. 
  1. Aweber – Email marketing platform 
  1. ActiveCampaign – Marketing automation platform that includes email marketing and small business CRM  

Book recommendation for entrepreneurs:   

  1. Buy Buttons: The Fast-Track Strategy to Make Extra Money and Start a Business in Your Spare Time – Nick Loper 

To set a good example for work, do business ethically, be of service to people, and do something in the world that will outlive him – Nick.   

Best way to connect: – Nick’s Podcast site  

Get Your Hopes Up and Maximize Your Dreams 🙂


About the author, Davis

My Dream of sharing inspirational success stories started many years ago and this Podcast is an amazing show that brings some of those conversations to light.

This show is dedicated to being a voice of encouragement to you because I believe God created you and I with a purpose to fulfill and I want to be here to cheer you on through this Podcast, our Blog and through our other channels of interaction via our comments section after each Podcast and Blog as well as on social media.

I love business and entrepreneurship and I truly believe you have greatness inside of you 🙂