Nick from Side Hustle Nation was born with an entrepreneurial spirit. He remembers selling baseball cards at the end of his driveway as a boy. He continued working hard through his middle and high school years, but the entrepreneurial bug really hit him in college.

As he earned a degree in business administration from the University of Washington, he signed up for a summer internship with a company called College Works Painting.

Nick says, “Basically they assign you a territory and it’s your job to go out and paint as many houses as you can over the course of the summer. The company also provided training on how to estimate and sell a paint job — and more importantly, how to actually paint.”

He says it became “crazy stressful” at times, especially with a bunch of 19-year-olds with paint sprayers. But he also remembers it being rewarding. “It was cool to look back from the sidewalk at the end of the week and see the transformation we’d made on the houses.”

Before his senior year, Nick took an internship with in Seattle. He says, “That was my first real exposure to online marketing, SEO, affiliate marketing and pay-per-click advertising.” This experience would help him later on when he started his own business.

But first, Nick graduated in 2005 and moved across the country. He took a job with Ford in Washington, D.C. “It was a cool experience to see the other side of the country and have a ‘grown up’ job,” says Nick. “I worked in their service and parts division, in a role that was part sales, part customer service, and part consulting.”

When he first told me about that experience, I thought that it was a brave move — relocating that far away from friends and family. Nick thought about the move differently: “Being 3000 miles away from my friends, family, and girlfriend turned out to be a blessing in disguise. Those first couple years of corporate life gave me a lot of free time in the evenings and on weekends.”

What I didn’t know is Nick already started a “fledgling little footwear affiliate operation” while he studied at school. Nick says, “My online business was using Google AdWords to direct people who were looking for specific models of shoes to the store I thought had the best selection and the best deal — with my affiliate link of course.”

The work became tedious for him, so as he toiled during the day in D.C., he started something new during his free time. “I had the idea to build out a comparison shopping site, like PriceGrabber or NexTag, which were big at the time, but do it specifically for shoes,” says Nick. “My theory was if I had ‘shoes’ in the domain, shoppers would see my search result as more relevant and click on it instead of those other sites.”

So, Nick decided he’d invest in this new business venture. “I contracted with a freelance development team I found on to build the initial version of the site,” remembers Nick. “It was called (really should have spent more than 5 minutes brainstorming domain names!) and later re-branded to The development cost $10,000.”

Nick had some money from his painting earnings, his day job, and a rental property he sold, which he says helped make the cost “a less daunting proposition.”

Leaving the rat race

Nick worked very hard over the next three years. Besides his day job, he invested “three years of nights and weekends building out the infrastructure for the site, managing the inventory, building ads, and developing relationships with my retail partners before I felt comfortable giving my notice at work.”

By that time, his company transferred him back to the west coast. He says “I’m not sure the site was earning enough to fully replace my salary, but it had at least a track record of making enough to cover my expenses and I was confident with another 40-50 hours a week to dedicate to it, I could get there pretty quick.”

Unfortunately, things took a bad turn. On his first day as a self-employed worker he experienced a serious setback. “My first day of self-employment was a rude awakening and perhaps a harbinger of the entrepreneurial roller coaster to come,” says Nick. “Google decided to shut down my advertising account, saying the sole purpose of my site was to drive traffic to other sites and that was against their terms.”

He just left a steady paycheck, and then he suddenly lost 80 percent of his traffic and revenue — just as the economy was self-destructing in the summer of 2008.

But his nightmare ended on a happy note.

“After 3 months of additional development, Google came back and said they’d made an error, and it was off to the races” says Nick. “Still, that experience sent a powerful message about diversification.”

During that time Nick started several other side projects, which he says “mostly flopped.” But a couple still endure, most notably Side Hustle Nation and The Side Hustle Show. But his shoe business doesn’t exist anymore.

Still, Nick says, “over the last few years, I’ve learned a ton from my awesome guests and have dabbled in recruiting, freelance writing, freelance editing, selling digital products, self-publishing, alternative investments, even cryptocurrency.”

And for our readers who are interested in earning more money or starting their own business, Nick happily provided this advice:

  1. Adopt an experimenter’s mindset. Give yourself permission to play around and test with an idea that interests you. After over 200 interviews, I think the most common differentiating factor between those that see success and those who stay on the sidelines is the willingness to try something out — even if it might fail.
  2. Recognize and celebrate your small wins. I call this the Side Hustle Snowball. You probably won’t generate enough income to erase your rent or mortgage right away, but what would it take to earn enough to cover your cell phone bill?
  3. The best way to earn extra money is to help someone else. Think about the skills and experience you already have and who you might be able to serve with those skills.

Keep hustling. 

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Brian Bienkowski

Brian Bienkowski


Bienkowski is a contributing writer and is the face of's 'By the Numbers' videos.

Career and Business, Lifestyle

economy, employment, Financial Profiling, income, office life, save money, small business

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