Robin Smith – Co-Founder & CEO,

Hailing from a rural Oklahoma town of just 300 people, Robin Smith is an unlikely startup founder and tech entrepreneur. But her business savviness, unique voice, and expertise as CEO and co-founder of WeGoLook — the world’s leading provider of on-demand workforce solutions for the enterprise — have skyrocketed her to success.

Robin founded WeGoLook in 2009 as a way to increase confidence in consumers purchasing online. It quickly became apparent that WeGoLook’s inspection and verification services were not only useful for consumers, but also a revolutionary solution for various industries. The B2B world has been WeGoLook’s focus ever since.

Robin has an extensive background in sales, eCommerce, and enterprise solutions that helped her develop WeGoLook. She is a thought leader in the gig economy, insurtech, and the startup/tech world. She speaks to audiences around the world, inspiring them to pursue their dreams, no matter how humble their beginnings.

Tell me about your early career.
My early career path took me down a curvy road. It was not defined from the beginning.

I started working for the Washington Post in sales for their cable division, CableOne, while in college. I ultimately did not complete college, as I had my first son in college and chose to focus on work and baby. It didn’t take long for me to realize my income was based on results and I quickly grew to a regional sales manager (moving to Joplin) then sales manager for a newly-acquired system in Columbus, MS. I was with Washington Post for almost six years then accepted a position with Cumulus Media as sales manager for NE Mississippi for a few years. My husband and I found out we were expecting my second son and moved back to Oklahoma to be around family. He passed away from a car accident eight months after my youngest was born and I chose to go back into direct sales versus management due to bandwidth. However, after a few years of working as a single mom with two sons, I decided I needed to step out on my own and create additional flexibility in my schedule in order to accommodate basketball and baseball practices, homework, etc. I started a consulting company (which was hard…taking the risky step of guaranteed income versus an idea). This was a good experience for me. I worked primarily for auto dealers and helped them set up their business development centers. This allowed me to learn about CRM tools, platforms, internet leads…it was knowledge I was able to apply to my thought process of how the workflow could happen when the idea of WeGoLook took shape.

How did the concept for WeGoLook come about?
I had a friend wanting to purchase a high-end projector on eBay and thought the seller was possibly misrepresenting the item. My friend stated, “I wish I had someone to go look at that for me.” After researching online, I couldn’t find a company providing those kind of services. Keep in mind, this was back in 2009, when everyone was buying on eBay. I thought it would be a great way to help people mitigate their risk when purchasing online.

For example, let’s say you wanted to purchase a pinball machine located in Kentucky but you are located in California. I wanted to allow people to: 1) order a report online 2) dispatch a “Looker” nearest the pinball machine in Kentucky to meet with the seller 3) have the Looker take current photos, video a working demonstration, take measurements, answer custom questions, even take possession of the asset to ship, etc. 4) deliver the report electronically to the customer to provide current information otherwise unavailable, allowing for a confident purchasing decision.

I launched out of beta in December 2010 with high hopes!

How was the first year in business?
My high hopes were somewhat dashed after realizing that I would need a multi-million dollar marketing campaign to get the word out about services WeGoLook provided. I traveled to eBay Motors in February 2011 but learned (appropriately) that I was too small and did not have the business or platform needed to partner.

The first year was quite challenging – focusing on a true business model. As you can imagine, there are a million things WeGoLook could do! Verify online dates, vehicles, heavy equipment, check on grandma in the nursing home, take photos of a grave site or vacation rental property, check to see if puppies were in a puppy mill, etc. WeGoLook can literally work for any industry, asset, and in any country. It keeps me up at night, in a good way!

What was your marketing strategy?
I had to revisit my thought process. I was putting too much energy into many buckets versus focusing on a few (hard for me to do). I began to focus on commercial property inspections (bulk orders/same template), auto inspections, and heavy equipment inspections and courier services. I created press releases, blog articles, SlideShare presentations, and more focused on headlines including keyword searches so others may find me. It was an all-out guerrilla marketing tactic but eventually began making traction.

How fast did the company grow during the first few years?
The company did not grow very quickly during the first few years, in my opinion. Others think that it was decent growth, as the business model was proven and we worked through software development and processes. Real growth began occurring in late 2013 and early 2014. Since then, we have hit a hockey stick and keep growing. I started with one employee along with myself and 4,500 Lookers. Today, I am at 135 employees and 36,000 Lookers across USA, U.K., Australia and Canada.

How do you define success?
Tricky question! Success to me is associated with contentment. Many people would say I’m successful, and, to an extent, I am. But I’ll not be completely content nor consider myself truly successful until I’m satisfied with where the company is. I have always “seen” WeGoLook in a global sense, running with a very robust and contingent workforce of Lookers (I have licensed drone operators, CAT adjusters, realtors, licensed diesel mechanics, notaries, etc.) which I can dispatch on-demand for our enterprise clients and individuals. See, my true goal is to provide the world with the greatest gig-economy pool of workers which are accessed through the WeGoLook platform and mobile application. We can match any task with any Looker. For example, if a bank is needing finance documents executed for a bank customer who speaks only Spanish, WeGoLook will solicit only a bilingual Looker who is also a notary and they can quickly (same day) meet with the bank customer at their home, place of business, or at a place like Starbucks. This is a very powerful service and I won’t be successful until this is in place.

However, in other areas of my life, I feel quite successful but I do believe success is associated with a certain level of contentment within yourself. Others judge success by how much money someone makes, what they look like, how successful their company is, how many people follow them on Twitter, etc. It’s important to understand how you define success for yourself and only work to attain that level of ‘success.’

What is the key to success?
#PureHustle is what I believe is the key to success. You can’t take a blank piece of paper or computer screen, an empty warehouse or office space then bring it to life without real thoughts, products, services, and people. And the hustle has to be a grinding, every day hustle. It can be exhausting and wonderful, all at the same time! There are days when you are on cloud nine and then there are days when it’s hard to get out of bed. Finding outside sources of motivation has always helped me. If thinking of my kids and our future isn’t enough motivation, I turn to my employees and Lookers…knowing that my decisions and hustle affect their daily lives. Being responsible for so many families is a lot to shoulder and there is a lot of motivation to continue the hustle surrounding these responsibilities.

What is the greatest lesson you’ve ever learned?
I finally learned to TRULY believe in myself. Things were going good and others were always believing in me but one day it dawned on me: I didn’t have to be an industry expert to be an industry leader. I had been doubting my experience within the insurance industry, the auto industry, the heavy equipment industry…talking to leaders within these verticals was sometimes intimidating. But I realized the founders of Uber and Airbnb did not have backgrounds in transportation or hospitality. However, they were able to create a much better consumer experience which was faster and cost less by utilizing technology. They turned big industries upside down almost overnight. I began believing that I could create better solutions utilizing technology as well – that I could be an industry leader with my product.

It’s a powerful feeling, when you truly and completely believe you can do something.

What are some of your favorite books?
I grew up reading autobiographies…real stories about real people. I still love learning.

I also really love movies – particularly those based on real events and war (Hacksaw Ridge, Braveheart, Gladiator, Dunkirk). It is inspiring for me to see how people are able to overcome adversity during times which display the very worst in people – to be able to conquer and display the very best in people. I find it motivational!

Tell me about one of the toughest days you’ve had as an entrepreneur.
Ugh. It was definitely early on when my silent partners came to the conclusion that I wouldn’t be able to ever let go of control (not true – I work consistently to delegate. I love to delegate) due to disagreements with a few leaders. One of the partners placed a person to be ‘in charge.’ This was really hard, because they were not involved with the day-to-day operations at all. They thought I didn’t know what I was doing because they were much more ‘successful’ at business than I was. I really hit a wall of depression – seeing the company taking steps backwards was really hard and I had no support. I almost just left it all. However, after several weeks of the person ‘in charge’ deciding they did not know what to do and losing our largest client due to continued poor report delivery, they asked me to come back and finally left me completely alone. That is when I was able to actually move forward quickly, but it was a very disheartening experience.

When faced with adversity, what pushes you to keep moving forward?
I think being widowed really put a lot in perspective for me. When I face adversity at work, I try to compartmentalize it and decide how critical it is. There is really nothing that compares with dealing with the loss of someone so I kind of take challenges and issues with a grain of salt. It takes a lot to keep me from not moving forward – it has to be truly critical. Then I stand back and break it up into pieces.

What advice would you give to young entrepreneurs?
I would tell young entrepreneurs to be resilient and persistent. Those are two of the keys to my success. I would also challenge others to NOT be so hard on themselves. We do NOT have to be experts in a specific area or industry to be a leader WITHIN that area or industry. It is our job, as entrepreneurs, to build the teams with diverse talent and experience. Building a successful business is definitely a team effort, so relax knowing that your talents are to build, coach, and lead this team to adopt your creation/vision. Just do it! I love that Michael Jordan is remembered for his many wins and not for the many losses or missed shots. I love that Babe Ruth is known for a historic home run hitter…yet he also struck out many more times!

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Interviews are conducted for research purposes by author Jason Navallo for his upcoming book, Underdog.

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