Love What You Do: Adam Wexler, CEO of SidePrize

This interview is presented to you by the University of Nebraska — Lincoln Master of Arts in Business with a Specialization in Intercollegiate Athletics Administration.

By: D.J. Podgorny, @DJPodgorny

Most young professionals passionate about a particular industry jump at any opportunity to get their foot in the door and take on the intense workload, just for a chance to climb the ranks within an organization. Adam Wexler, CEO and Founder of SidePrize, on the other hand, combined his fascinations with work in a different manner.

As a business student at the University of Georgia, Wexler was given a common piece of advice: follow your passions. For Wexler, this equated to music and sports. With the ‘digital revolution’ of the music industry in full swing, companies like Pandora, Shazam and ReverbNation were just starting to gain significant traction. Wexler decided to double down on his love for music.

As a senior in college, Wexler founded Vital Airwaves, a company that fused the best local music with excellent local cuisine, running cross-promotion between the two. Wexler ultimately closed Vital Airwaves in favor of his new, fully digital music discovery website: Go Rank ‘Em.

Wexler spent the final semester of his senior year building Go Rank ’Em and applying for jobs at some of the top, up-and-coming digital music companies. With graduation looming, Wexler made the executive decision: go all-in on his startup.

Wexler spent the next three and a half years building Go Rank ’Em from the ground up. While the startup wasn’t considered a financial success, Wexler attributes many learnings to his time founding Go Rank ‘Em.

“We didn’t make any money off of Go Rank ’Em, but I went through ‘The School of Hard Knocks’ and learned on the fly what it was like to build a company. I learned more exposing myself to real world situations than I would have inside of a classroom. Though the company was a failure at the end of the day, it was the marketing that we did for Go Rank ’Em that led me to start my next company.”

After more than four years of working on his passion project, Wexler decided to leverage the marketing knowledge and expertise he built to found a platform for scaling influencer marketing. Wexler founded Insightpool as a means to productize all of the social media efforts he was doing by hand to grow Go Rank ‘Em’s user base. By connecting with popular music bloggers and influencers, Go Rank ’Em was able to project their message to a much wider audience. Insightpool was created to do this for large companies, at scale.

Insightpool proved to be a resounding success, bringing on clients everywhere from Coca-Cola to NBC Universal to UPS. The company quickly grew to more than 50 full-time employees and worked with Fortune 500 companies across the globe. As the company began to grow, Wexler slowly began phasing out of his day-to-day role, ultimately leaving Insightpool after three and a half years to pursue other ventures.

Due to his success with Insightpool, Wexler began to earn credibility as a thought leader within the social media space. His talents and knowledge caught the attention of newly appointed Atlanta Hawks CEO Steve Koonin. After a conversation over brunch, Koonin offered Wexler a position as a digital and social strategy consultant for the Hawks.

Wexler was elated to reconnect with his interest in sports and served in this role with the Hawks for six months, helping to position the franchise as digital leaders. In addition to working with the Hawks on a part-time basis, Wexler also began developing his latest startup: SidePrize.

SidePrize was originally constructed as a solution to help fantasy sports commissioners manage their league dues, seamlessly and stress free. The business model evolved after a couple of months of operation when the team realized that the true value was in finding ways to keep fantasy sports players engaged throughout the season.

SidePrize is currently solving the same problem sites like FanDuel and DraftKings are attacking, but in a novel way. Instead of creating a new game that requires users to spend time researching and drafting new players each week, SidePrize provides an avenue for users to place weekly wagers on their standard fantasy matchups.

This notion of legal wagers in skill based competitions, chopped up into discrete chunks throughout the season, is exactly what landed SidePrize a spot in the inaugural Dodgers Accelerator with R/GA class in 2015. The team has continued to build off its initial success, earning three Fantasy Sports Trade Association awards, including ‘Rookie of the Year’ honors at the 2016 Winter conference.

For Wexler, there was no secret to his success in the entrepreneurial world. It has all came down to taking the leap of faith and putting in the hard work.

“Become an athlete in a professional context.”

“I was willing to put in the work, the blood, sweat, tears, over nights and weekends to get a company started. When you’re pursuing your own company, even if it is a colossal failure, you’ll learn a ton. You learn almost every facet of a business when it’s all on you. I’m not saying entrepreneurship is cut out for everyone, but I do think the people who are exposed to it, even if they do fail, will become much stronger as a result. And, if you’re observant and you put yourself in enough of the right situations, you’ll land in a great spot.”

Wexler understands that not everyone has the capabilities or opportunities to succeed as an entrepreneur. Be that as it may, he encourages all young professionals to get involved with startups early on, in any way they can.

“Not everyone is cut out to be an entrepreneur, but there are plenty of people that can be cut out to be those who follow the entrepreneur. There are a lot of employees out there, both at big and small companies. To me, where you’re going to get exposed to the gamut, especially as a young person, is in startups. At a young age, go work for the small companies and really hone your general skillsets. Become an athlete in a professional context.”

When it comes to following your passions, Wexler takes issue with the advice he was given as a college student.

“If everybody were follow their passions, nobody would be flipping burgers at Shake Shack and Burger King. The better way is love what you do. I do think there are people who are flipping burgers that love what they do, they turned it into a fun, enjoyable job, whereas nobody would grow up and aspire to do that as a living. It’s about the proper mindset.”

“Coming out of the gates in your career, you should focus on loving what you’re doing and hopefully someday it will amount to being able to do what you love.”

“In a weird way, it worked out for me as I went down the path of finding opportunities and ultimately it led me back to an area of interest, namely sports. Love what you do along the way and if you get enough experience under your belt and have success, you can find your way back into that industry of doing what you love. Coming out of the gates in your career, you should focus on loving what you’re doing and hopefully someday it will amount to being able to do what you love.”

For young professionals interested in pursuing careers in sports, Wexler encourages people to strive for excellence in a certain skill, then use that as a method to break into the industry down the road.

“If you set your goals at the being the best at something, be the biggest expert on certain subject matters, often times those can funnel back into the sports industry. Aspire to be an expert in a domain such as marketing, sales, analytics, etc. Ultimately, you can get back into the sports industry, later down the line and come in at an executive oriented role rather than working your way up. I believe it also gives you a holistic perspective. Some of the most successful people in sports have come from other industries and are able to apply everything they have learned outside of sports.”