Episode Details

Gideon Shalwick believes there’s one trait every entrepreneur needs, and it’s not persistence, a strong work ethic, or creativity. It’s self awareness. His own desire to better understand himself has led him down a winding road of serial entrepreneurship and self-exploration.

It’s what first inspired Shalwick to drop out of the 9-to-5 club early in his career, move to another country with his wife, and start fresh. The pursuit of his true calling led him to publish a successful ebook in 2006, and two years later, develop a blogging training product that boasts over 40,000 subscribers. Meanwhile, Shalwick was also building up a personal brand as an expert in video marketing.

But his journey didn’t stop there. In 2012, Shalwick founded video captioning service Splasheo, which has become a major source of passive income. He followed that success in 2014 with Veeroll, a SaaS company that automates the production of video ads for YouTube, Instagram, and Facebook, and now dominates the video advertisement space.

While Shalwick saw great success with these companies, he found that tug of self-discovery pulling at him again. He realized he had become so caught up in the startup world that, in the process, had forgotten who he was.

So he decided to walk away from the projects he spent over a decade building. Now, he’s in a period of self-rediscovery and is sharing his entrepreneurial wisdom with others while plotting his next move.

Five years into his career, Shalwick decided to start over, for the first time. He had graduated with an electrical engineering degree from the University of Canterbury in New Zealand and immediately recognized that he didn’t enjoy working for someone else.

In an attempt to try another path, Shalwick got his master’s degree in engineering management, which focused more on the people side of business. Still, he felt frustrated by his job.

“I don’t think there was any job in the world that would allow me to live out my potential the way that I wanted to, so I felt really stuck,” Shalwick says.

He turned to his wife and suggested that they quit their jobs, move to Australia, and start from scratch.

At first, the plan was for Shalwick to find a job in Brisbane as their ticket in. But three months later, he still hadn’t found employment. He asked his wife to try applying for jobs as well and,  within a week, she had three offers. While this allowed them to successfully relocate, Shalwick still had no idea what to do with his own career.

Shalwick began reading books on entrepreneurship, with the hope that they would point him in the right direction. It was Rich Dad, Poor Dad, which talks about the importance of building up an asset, that eventually struck a chord. Shalwick wondered how he could build up his own asset and started to explore a variety of options.

He considered everything from franchises to a dog-washing business, but ultimately ended up attending a book-writing course that gave him his first taste of entrepreneurship. In 2006, Shalwick wrote and sold a personal development ebook for $47. The title? Millionaire Dropout Secrets.

“I blush when I think about the title, but I have an excuse,” Shalwick says. “The course taught us that titles with the words ‘secrets’ and ‘millionaire’ in it do really well. So I came up with the title Millionaire Dropout Secrets...I wrote it as a reporter, looking at everyone who dropped out of the system and became successful.”

The ebook was a huge success. The instructor who taught the course offered to help promote the product to his database of 10,000 people. An email was sent out on a Friday night and, by Saturday morning, Shalwick’s ebook was selling like hotcakes. In fact, he sold enough copies to where he felt extremely optimistic about the idea of selling digital products from the comfort of his home for the rest of his career. Sh