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John Crossman: Career Coach Mentors Peers, Next Generation

John Crossman

Counselor, politician, real estate executive and pastor. When John Crossman’s CEO career transition coach gave him his top four matches for the next stage of his career, it wasn’t a hard choice for the former chief executive at Orlando commercial real estate agency Crossman & Co. In fact, he didn’t have to narrow it down at all: “I decided to embrace all of that,” he said with a laugh.

Soon after, he founded two new companies: Crossman Career Builders and CrossMarc Services. He tackles his new roles in stride by mentoring young professionals and college students at Crossman Career Builders and advising established CEOs at CrossMarc. During a time in history marked by turmoil and uncertainty, his skill for having the hard conversations — like those about racial inequality and mental health — has created a model for executives in every sector of business. 

New Companies 

In 2019, Crossman stepped down from his 14-year leadership role at Crossman & Co., which was founded by his brother, Scott, in 1990. Leaving the successful firm that he helped grow into a top-ranked commercial property management organization was a tough decision, but there were more pressing matters at hand for Crossman. Both his wife and his mother had recently fallen ill, and with two teenage daughters at home, he decided his time would be best spent prioritizing the women in his life for as long as they needed him. 

“Then, basically, two things happened that changed my course,” Crossman said. “After six months, both my wife and my mother made it clear they didn’t need me around all the time —which is a nice way of saying, ‘You’re hovering.’ That, and I found the end of Netflix.” 

He decided to turn his attention from caregiving and watching TV to a new phase of his professional life: career coaching. After a conversation with his executive coach, his two new companies began to take shape.

He founded Crossman Career Builders first, to focus on coaching and mentoring college students and young professionals in the commercial real estate industry — a realm in which he had already gained plenty of experience by speaking at college commencements and programs across the country. 

Soon after, as the COVID-19 pandemic left more and more business executives looking for guidance, he launched CrossMarc Services, where established CEOs could come to him for insight. CrossMarc has since been retained by several Fortune 500 companies, as well as owners of large real estate portfolios. 

Each of the two companies has expanded and evolved in the past year, now providing coaching and corporate consulting on topics like mental health, racial inequality and suicide awareness. 

Shaking Up the Status Quo

At the beginning of his professional journey, Crossman recalls being one of the only 20-somethings in an industry dominated by his older peers. But for the son of a pastor and civil rights leader, the instinct to lead quickly propelled him toward a mentorship role. “I grew up in a household that was big on purpose and community involvement.” 

His career would turn out to present plenty of opportunities to continue that trajectory. Early on, he was invited to present at a Florida State University (FSU) program titled “If I Were 25,” which the college says “brings leading voices from across the nation and industry segments to the FSU Real Estate Center’s platform to talk to students about their work, their career path and how they’ve dealt with adversity and experienced success.” The problem? Crossman was only 24 at the time. Rather than lose out on his insights, FSU changed the program’s name to “If I Were 21” — a change that has stuck for more than two decades.

That was far from the last time Crossman would change the status quo in his industry. “I’ve had an interest in social issues pretty much my entire adult life. But now these new companies have allowed me the time and focus to give me a better platform to express my ideas.” 

Constructing Healthy Careers

As he traveled the country, fine-tuning his speeches in front of many promising future professionals on college campuses, Crossman whittled down his advice in a guide he called The Top Five Ways to Get Fired and The Top Five Ways to Keep From Being Fired. His words of wisdom have since been turned into the book Career Killers, Career Builders:
The Book Every Millennial Needs to Read!
and it was upon closer examination of the teachings in the book that he realized something very interesting. 

“I wasn’t talking about being late for work or dressing appropriately, I was talking about these things that could end people’s lives,” he said. “This was not long after the Great Recession, during which five people I knew committed suicide. And think of Kate Spade and Anthony Bourdain. Many times, with really successful people, there is a deeper wounding. Sometimes they are even overcompensating for that deeper hurt they may not have dealt with. 

“I personally have struggled with clinical depression. It was terrible, and I would not want anybody to go through that, but I’m glad for the empathy it’s given me. The more I lean into understanding all of these things — loss and greatness and talent — I realize it’s all linked. I don’t know how to not address it. It’s part of my story and it’s part of a lot of people’s stories.”

Crossman incorporates these insights into his work with people he mentors. In February 2020, Crossman Career Builders was the largest fundraiser for the Central Florida Suicide Walk.

A Time for Empowerment

This year has also thrown another one of his passions into a harsher light. The pandemic-related challenges of 2020 presented a kind of reboot for everyone, Crossman explained, forcing perspectives to change not just on career decisions, but on issues of a much grander scale. With the death of George Floyd in May 2020 at the hands of Minneapolis police, Crossman found more and more of his peers compelled to turn their focus toward racial inequality and diversity. 

For Crossman, the issue has always been deeply rooted and holds the key to a healthier, more equitable world.

“At the end of the Civil War, former slaves were told they could vote, but they had to own land to vote and it was illegal for them to own land,” Crossman said. “Land ownership has been used to hold minorities and women down for so long. Women couldn’t even own real estate in the state of Florida up until the 1970s. It’s all linked.” 

What seems hardest for some to grasp, he said, is that it’s not the people in the real estate industry or their intentional actions who perpetuate these practices, “it’s an example of institutional racism. The whole system is set up this way.” He is determined to change that. 

For his part, Crossman has made it a point to provide scholarships for students at historically Black colleges and universities (HBCUs), including the first endowed real estate scholarships at Florida A&M University (FAMU) and Bethune-Cookman University. Other scholarships include the first endowed real estate scholarship at Valencia College for Hispanic students and an endowed real estate scholarship at Florida State University for women and minority students. 

Most recently, Crossman partnered with Kelley Bergstrom, chairman of Bergstrom Investment Management, to provide a full scholarship at the University of Florida master’s in real estate program for graduates of FAMU.

“I am currently working to get 10 downtown Orlando law firms to endow scholarships at the FAMU College of Law,” Crossman said, a goal he describes as an uphill climb. “A lot of law schools and real estate CEOs are not recruiting at HBCUs like FAMU and are missing out on this incredible talent. We need to make that effort at a collegiate level, and we still have a long way to go.” 

Dismantling these barriers to access has the potential to create a ripple effect that makes the hard work and sacrifice more than worth it. “Diversity is not about lowering the bar, it’s about widening the net,” Crossman said. “When you increase diversity, you have all your best players on the field.”

Crossman also knows real estate is one of the most reliable means of accumulating and expanding personal wealth. “Look at it this way: If we are on a highway full of other experienced drivers, we are all a lot safer on that highway. The more educated a population is, the more people have the means and financial literacy to navigate their world, the better off our whole society will be.” 


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About the author

Meaghan Branham

Meaghan Branham is the managing editor for i4 Business, where she oversees the company’s digital media strategy, handles client relationship marketing for the print and digital magazines, and serves as one of the publication’s lead writers. A native of Brevard County, she splits her time between Central Florida and Nashville, Tennessee.

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