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Heartland Entrepreneur: 1 Woman's Journey to Global Startup Success Neither age, nor location, nor gender defines or limits an entrepreneur.

By Peter Daisyme Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.

Robin Smith
Robin Smith

The success of startups in recent years has always seemed to have some geographic connection to a hotbed of entrepreneurial activity comprised of eager young guys with the next best idea.

However, the scene is now changing and the online environment is proving that anyone out there, regardless of his or her location -- and gender -- can live the entrepreneurial dream.

Related: On Women's Entrepreneurship Day, We #ChooseWomen

One of these new entrepreneurs is Robin Smith, founder and CEO of WeGoLook, a company of more than 30,000 on-demand field service agents (known as "Lookers"). The Lookers perform inspections and tasks for insurance, financial services, auto and fleet inspections, heavy equipment verifications and more across the United States, the United Kingdom, Canada and Australia. The company was recently acquired by Crawford & Company.

I met Robin at a recent conference and wanted to share her amazing story. Robin fell in love with the word "entrepreneur" while growing up on a farm in rural Oklahoma. She was asked to spell the word during a spelling bee in elementary school. When she looked up the word, she said, she was surprised that people could actually create their own business and life's path.

It dawned on her that that was exactly what her parents had done with their farm.

Robin was inspired to become an entrepreneur. She began making and selling yarn belts on the playground. From there, she recruited friends to make more -- at least until the school's principal shut down this burgeoning startup gig.

That action didn't stop her, because she went on to create WeGoLook.

Not that there weren't barriers: As a 45-year-old woman from the Midwest, Robin found that her challenge was not about competing, but surviving. As she told me, "It's been more of a competition with myself, working to develop a new-to-market technology platform without an engineering background. I had to learn to step out of my comfort zone, become personally innovative and work towards finding resources and ways to make it all happen."

Another challenge was funding, because Oklahoma has fewer investment groups and funds available. Yet, Robin was able to stand out because she selected a unique niche where she could be that big fish in a little pond. And, she spent considerable time researching the funding that would help grow her startup into a full-fledged business.

Don't doubt yourself

Throughout the journey to her present success, Robin said, she has learned a lot about what it takes to be an entrepreneur. Her greatest advice? Not to doubt yourself. "It is easy to doubt your decisions or wonder if you're making the right choice," she told me. "It is easy to think, "Let me work on this longer in order to gather more data.' This is especially true with a service that was one of the sharing economy pioneers.

"Then I realized that the founders of Uber and Airbnb didn't have an extensive background in transportation or hospitality [either] . . . so I didn't have to be an industry expert to become an industry leader. I just had to put the right team together.

"When I became 100 percent confident with this belief, it was much easier to make solid decisions."

Besides self-doubt, Robin said she struggled with technical aspects like understanding coding options. She realized she needed not just a dedicated IOS and Android developer but a good mentor to guide her toward the right software development team.


Then there was the fact that she was introducing a new service in this new area, the sharing economy. In 2010, this concept was still unfamiliar, but became much easier to sell after Uber took off.

However, because WeGoLook didn't fit into a typical market category, Robin had to get creative with SEO and guerilla marketing tactics, especially given her lack of money for a marketing campaign. Over time, her tactics produced organic, inbound customer leads. While many entrepreneurs look for instantaneous results, Robin learned the importance of patience in the startup world.

Related: U.S. Is No. 1 for Women Entrepreneurs, But There's Still Room for Improvement

Because time and patience are so integral to the process, motivation can become difficult to muster. Yet, today, Robin said she encourages other entrepreneurs to keep going no matter what. "There were days where I wondered why I chose to continue to scratch and claw away at gaining any ground, especially where I would lose ground.

"Yet I always believed with my heart and soul that WeGoLook would be providing 'looks' anywhere in the world; and my Lookers, which at the time included my two sons and a small group of employees, kept me motivated. I had to always find the best in everything, and that took some growth on a personal level."

While those moments were hard enough, she said, nothing prepared her for the most difficult challenge: A few years into building the business, Robin was struggling with hiring the right floor manager. Her partners thought she couldn't find the right fit because she was having a hard time letting go of the control. But that was actually exactly what she wanted to do.

Partnership difficulties

Robin's partners hired a new floor manager while she was on vacation and proceeded to place another friend in charge. When she returned, she wasn't allowed to even attend their meetings. This left her feeling disheartened; and she almost left the company.

However, after WeGoLook lost its largest customer at the time -- Robin blames the-then new management strategy -- she was asked to return. Eventually, she says, she did find the perfect leadership team member; and the company flourished

That difficult period taught her about the challenges of working with business partners and determining the best path for the company.

Pivot opportunities

Another big lesson Robin describes is that there comes a point in time where a pivot in the business is necessary. In fact, she believes that every entrepreneur has to pivot at some point from the original concept, even if only slightly.

"I started WeGoLook with the individual consumer marketplace customer in mind," she said. "The ability to dispatch a Looker on-demand to take current photos of the item, video a working demonstration, answer custom questions and take it to a shipper on your behalf seemed like a very valuable service."

In 2012, a breakthrough occurred: A bank the company had begun working with on performing commercial property inspections liked WeGoLook's report product and service so much that it requested other large banks to utilize the product as well.

"This increase in business really generated the idea to start offering businesses a custom report with a nationwide footprint, and that's when we pivoted and began focusing on on-demand B2B services."

That was WeGoLook's pivot, Robin said: "The idea of continual change as part of always looking into the future is a must if [entrepreneurs] want to sustain and grow their businesses," she said.

Her own Looker community includes diverse people with varied skillsets who can be dispatch on-demand to any location. "We have licensed drone operators, mobile notaries who speak Spanish and real estate agents on our team," she said. They follow instructions provided on the company's mobile app, and capture required data. "This ability for an enterprise client to quickly and cost effectively have a custom service performed is invaluable."


In recent months, Crawford & Company, one of the world's largest TPA firms, acquired a majority interest in WeGoLook, enabling it to expand to more than 70 countries and access its considerable resources. This partnership is helping the company Robin built to bring innovative solutions to the insurance industry and the finance and auto verticals.

Related: Why Women Entrepreneurs Can Do More With Less

From a little girl at a Midwest spelling bee, to a successful global entrepreneur, Robin Smith proves that age, gender and location need not factor in to defining an entrepreneur. Instead, the requisite factors are mindset, passion and determination.

What's more, the lessons Robin shares can be applied to anyone out there considering an entrepreneurial career, or someone who already has his -- or her -- sleeves rolled up and is ready to begin.

Peter Daisyme

Entrepreneur Leadership Network® Contributor

Co-founder of Hostt

Peter Daisyme is the co-founder of Hostt, specializing in helping businesses host their website for free for life. Previously, he was co-founder of Pixloo, a company that helped people sell their homes online, which was acquired in 2012.

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