Best in The Biz: Leap of Faith Paying Off For Evan Stewart

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Over the past six years, Evan Stewart built a real estate career that would be the envy of many.  A successful agent at Compass with a rapidly growing portfolio, he seemingly could have continued for years and lived a pretty comfortable life.

But Stewart says he legitimately felt that God needed him somewhere else. He considers himself blessed with a gift for identifying ambiguous constructs in business. And while he still enjoyed real estate, he ultimately felt unfulfilled because he could not use that gift he had been given.

Nurturing an Obsession

Last summer, Stewart began phasing himself out real estate.  He stopped accepting new business and began closing out his remaining projects so he could turn his attention to a new venture — Obsessed Academy.

“Obsessed Academy is a company that really scales and helps people build what is inherently un-scalable,” Stewart said. “We work with companies that have an alternate purpose to better the world around them and use their gift of knowledge to do that.”

Evan Stewart left behind a successful career in real estate to launch Obsessed Academy.

Those companies include professionals like Realtors, financial planners, and other fields that require someone providing solutions, not just selling a product. Stewart helps them focus on things like building structures and streamlining processes that will ultimately make their business more successful. 

One of his earliest clients was a real estate professional looking to take his business to the next level. Over the course of a year and a couple of months, that client changed affiliations, started his own brokerage that he is now rapidly expanding.  This year, he’s on track to go from netting $280,000 to over $1 million.

“I’m putting out what I wish I’d had when I was starting my own business,” Stewart said. 

Taking The Leap

Of course, successfully jumping from one career to another doesn’t happen overnight. One of Stewart’s long-held beliefs is that you build a business to exit it successfully.  He started doing private consulting on the side about three years ago. In November 2018, he began more aggressively building the book of business that would become Obsessed Academy. Last summer he took his leap of faith.

There were definitely some nerve-wracking moments along the way. Stewart had started businesses before and began to remember just how challenging the process can be. At one point he found himself spending $50,000 a week in his own money. The costs continued to rack up as he worked towards his first Success Conference. When the time came, he was worried about just how much was investing in the event. The following day, he earned double what he had put into the event. The same thing happened the following day.

“At that point, I said, ‘OK — we’re moving,’” he recalled.

Stewart is now earning clients from across the globe. Last year’s conference drew 100 people.  This year he’s on track to sell out 1,200. His goal next year is to move to the 5,000-seat Kay Bailey Hutchinson Convention Center, and after that, The Ford Center at The Star in Frisco. 

While some people may have negative connotations of the word “obsessed,” Stewart emphasizes that there are both healthy and unhealthy obsessions. The key is to recognize and overcome unhealthy obsessions to create a cycle of healthy obsession based on having the right mindset and discipline. 

“Our mission is to leave a significant footprint and impact on the world through our ability to impact those that have a platform and an audience, and are doing pretty incredible things,” he said. 

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Joshua Baethge

Joshua Baethge is a writer, editor and general wordsmith who has written for a variety of media outlets. At, his primary focus is agent migration where he catches up with real estate professionals on the move. A native of Houston, Josh originally came to the DFW to study at the University of North Texas. He graduated many years ago but never left the area. Today he lives in the ‘burbs with his wife and two young kids.

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