Let’s learn a few things from Nick Loper, as he shares the top 3 mistakes he made as a side hustler.

Nick Loper is a side hustler, an a online entrepreneur and lifelong student in the game of business. He is the founder of Side Hustle Nation, a weekly podcast teaching a growing community of part time entrepreneurs (Side hustlers).

Let’s learn a few things from the king of “side hustle” himself… Nick Loper.

Q: What were the top 3 mistakes you made starting out with your business, and if you could start over what would you do differently?

1. Hiring Ineffective Web Developers

This is my number 1 mistake because of how costly and frustrating it was. In total, I lost more than $10,000 on incompetent, over-promising, under-delivering web developers for a large-scale project.

When my site was due for a redesign, I was unhappy with my current development team. Their communication was horrible and I felt like they had some technical shortcomings so I shopped the project around on Elance and some other platforms.

Ultimately I was wooed by a small company in Minneapolis who assured me they could do the job. I was really excited because their price wasn’t much more than some of the overseas bids, and I knew we wouldn’t have to worry about any language barrier causing misunderstandings or miscommunications.

However there was one MAJOR misunderstanding, and that was that I actually expected the work to get done! These guys were the absolute worst, making my concerns about the original developer’s poor communication habits look like nothing at all.

Months went by and deadlines came and went, always promising an update soon, or next week. Those updates never came and we ultimately had to part ways, and I had to start the project over completely from scratch.

The worst part? The owner of this development firm convinced me to do business with him outside of the Elance platform — meaning when he flaked I had ZERO recourse.

Huge, painful, stressful mistake that ended up costing almost a year to fully recover from. And that business has never really been the same since.

Now I run a site called VirtualAssistantAssistant.com, which aims to help others avoid the same outsourcing mistakes I made.

"Keep calm and Hustle on" - Nick Loper

2. Not Hiring / Scaling Faster

Because my business was a side hustle, I had only nights and weekends to work on it. But business was good and I seemed to have a profitable system for growth if I only had more hours to execute on that system.

In hindsight, what I should have done was brought on a team member and trained them so I could effectively “duplicate” myself and my efforts.

It took me a long time to get over a ton of excuses for not getting help. I was afraid an assistant or intern would try to steal my ideas. I was afraid they wouldn’t do as good a job as me. I was afraid of opening the doors to my accounts to someone new.

Eventually I got over those fears and was able to bring on some outside help, but it was definitely scary at first. Had I done it earlier, I could have capitalized on a unique period of opportunity in the business, focused my attentions on higher-level strategic projects, and earned more money.

3. Pursuing Projects I Didn’t Really Care About

My entrepreneurial resume is filled with abandoned, failed, and other half-assed / half-brained projects I started but never really gave full attention to.

One example is a poorly researched site on handbags and luggage. If I’d done my homework, I might have found that the competition was too widespread and the technical aspects too difficult to create a truly valuable resource.

Later, I tried to build a wine-related site. The problem was I know nothing about wine other than I live in California and like to drink it. That lack of passion for the subject matter showed in the content and the site really had no “reason to exist.” It was a lame attempt to sell wine gifts but didn’t really add any meaningful value to anyone’s shopping experience.

After some soul-searching, I uncovered something I really DO care about — and that’s part-time entrepreneurship. It’s a lower-risk brand of starting a business than you’ll typically read about in Inc. and Forbes, but it’s something with a broad appeal and how I got my start in business.

The side hustle economy is HUGE and something I’m excited to be a part of, helping people accelerate their financial fortunes through part-time businesses they love.

“Keep calm and Hustle on” – Nick Loper [Tweet it]


Connect with Nick Loper

Twitter @Nloper


  • When it comes to mistakes, you’re definitely not alone. Side hustler or not, we all go through them.

    Thanks for sharing Nick and keep the hustle on.

  • Thanks for having me Herby! So many mistakes… hard to pick just 3 🙂