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Origin Stories: The Air Force Taught Trevor Hightower To Do Common Things In Uncommon Ways

This series delves into the myriad ways people enter the commercial real estate industry and what contributes to their success.

Trevor Hightower's career has pivoted a few times, but since that first real estate finance class taken as an officer in the Air Force, he's been hooked on the idea of place. As he moved from working as a financial analyst at an industrial REIT to executive office leasing positions, and later to running a coworking brand in apartment buildings and his current role leading a multifamily experience offering, he centered his career around Winston Churchill's saying that "we shape our buildings; thereafter they shape us."

Craftwork founding partner Trevor Hightower with his son, Chase, at an Air Force football game.

Hightower began his CRE career in 2007 at Ridge Property Trust. After stints at office REIT Parkway Properties and CBRE, he started Workflourish, which built coworking spaces in multifamily buildings. In 2018, he co-founded Craftwork, partnering with multifamily properties to reimagine the lobby with coworking spaces and coffee shops and to improve the resident experience. Craftwork has partnerships in place to expand from one to eight locations across Texas in the next six months.

"The stores, offices, homes, museums, parks, neighborhoods, mix-use places we inhabit are constantly shaping us in obvious and not so obvious ways," Hightower said.

Bisnow: How did you get introduced to CRE? 

Hightower: While I was still in the Air Force, I took a real estate finance class at night as part of my grad school program. It was the one asset class that seemed the most intuitive to me. Let’s be honest — it was the one I could actually understand! I just got the tangible nature more than I did stocks or bonds. A good friend, Gray Bouchilon, who has since become an incredible leader in CRE, introduced me to a job as a financial analyst for Ridge Property Trust in LA.

Bisnow: What was your first job in CRE? 

Hightower: I worked as a financial analyst and project manager for Ridge Property Trust, a developer doing big-box industrial development in the Inland Empire. I had an amazing boss and mentor named Dennis Rice. He took me under his wing and took me into every meeting, empowering me to learn every step of the way. When the financial crisis of 2008 hit, I think because I begged and pleaded that I would do anything, including sweep the floors of our development, I was able to stay on the small team. Luck is what happens when preparedness [meets] opportunity, and I was really lucky that I got to learn in such a difficult time in the industry.

Bisnow: What kind of education, certification or official training do you have in CRE? How critical was it to landing your first big role? 

Hightower: I had graduated from the Air Force Academy and had experience as an officer in the Air Force. That experience, however, did not have any direct tie to the skills that a real estate developer would need in an analyst.  I got an MBA, which gave me some general business knowledge, but it was the specific financial modeling classes I took prior to my job at Ridge which gave me the specific skill I would need at my first job. What is most exciting is these classes are available to anyone and at much lower cost than universities. I highly recommend this type of specific learning. 

Craftwork Coffee Co.'s Trevor Hightower, No. 44, playing football for the Air Force Academy.

Bisnow: What is one skill you wish you had coming into CRE?

Hightower: The “skill” of patience has never been an easy one for me to obtain! In life and in our real estate careers, there’s no elevator. We have to take the stairs. Every day is a new opportunity to take one more step to our growth and development. There is literally an endless amount of growth and competency we can develop. I think very early in my career, I was naïve to just how little I actually knew. I think at my current stage, I am just at the beginning of how much I need to learn and grow to help my company. 

Bisnow: What were you doing before you got into CRE?

Hightower: I was an officer in the Air Force at Los Angeles Air Force Base. I was a contracting officer working with Lockheed Martin on the Atlas V launch vehicle. It was right when Elon Musk was starting SpaceX. I remember reading an article about his reasoning from the principles, saying that he could build the same rocket that Lockheed was for a fraction of the cost. I remember thinking, “he’s right,” while most in the aerospace industry said he was crazy. I’ll never forget that, and it created in me a love of outsiders making industries better and a deep respect for him as an entrepreneur.

Bisnow: If you changed careers, did you bring anything with you from your past career that has helped you thrive in CRE, or, on the flip side, anything you had to unlearn in order to succeed here?

Hightower: The Air Force really teaches you to do the common things in an uncommon way. The most small details are extremely important when you’re in the military. Part of my entrepreneurial nature rebelled against this, at first. But it got ingrained in me. How you do anything is how you do everything.  Doing the common things in an uncommon way is how you really set yourself apart, particularly if you are very consistent. 

Craftwork founding partners Riley Kiltz and Trevor Hightower

Bisnow: Can you remember a moment where you felt in over your head or you worried this industry wasn’t for you? Did you ever think about quitting? What changed? 

Hightower: There are moments I still feel this way! In my CRE career, I have switched to three different asset classes and multiple disciplines, from finance to office leasing to managing a group of talented brokers to starting and running a coworking space to Craftwork. Each new step I did felt like I was over my head. I think what I learned is that’s OK. It's actually normal. I learned to not pretend like I knew something that I didn't. To ask many “stupid questions.” It turns out more people in the room were actually thinking the questions. 

Bisnow: What were your early impressions of the industry, good and bad? How has your impression changed?

Hightower: When I first started my career, I really didn’t know that much. I have found that some of the highest character people are some of the most successful people in real estate. This may go against some people‘s perception. Of course there are exceptions, but real estate generally rewards men and women of really great character, great work ethic, and who create more value than they take. There are some of the highest character people I have met who are leading the industry. 

Bisnow: Have you had a mentor or sponsor? How did that person shape your future in CRE? 

Hightower: I am really fortunate to have had a few mentors. If you’re reading this and starting out in real estate, I could not recommend highly enough you intentionally finding and nurturing mentor relationships. As an aside, my advice would be to always take detailed notes of your conversations and follow up with your mentor about how you have implemented or changed something because of their guidance. It makes their time and impact on you feel honored. 

My mentors have been Mike Fransen at Parkway Properties, who is one of the most principled leaders I know. John Holland, who led me at CBRE and is the definition of a Level 5 leader. Dean Macfarland, who is one of the wisest men I know and is an adviser and investor in Craftwork. John Marsh, who has helped me become a better placemaker, but also a better man.

Craftwork's Trevor Hightower with his wife, Tyler, and their children, Chase, Grace and Elle.

Bisnow: What is a key lesson someone taught you, either kindly or the hard way?

Hightower: The importance of partnership. Your success in any industry will, in large part, be connected to the people you tie yourselves to. You can’t do this alone. It is better to be with a team to complement your weakness and strengths. I truly believe I have the best partner in the world in Riley Kiltz. Riley is so strong where I am weak. His character has always outpaced his giftings. And his giftings are some of the best I have ever seen (which tells you about his character). I am a better professional and a better person because of Riley. 

The most important partnership is your spouse. I married my college sweetheart. Tyler is my best friend and rock. Talk about strong where I am weak! I don’t have a career without her. 

Bisnow: What do you warn people about when they join the industry?

Hightower: Play the long game. Don’t take shortcuts. All the best things in life compound. So, do the small things daily that build your reputation, your knowledge, your competency.

Also, know that the industry is changing.  Developing a competency and understanding in technology and operations will be important for most asset classes.

Bisnow: If you could do your career all over again, what would you change?

Hightower: Like Air Force basic training, I wouldn’t want to go back and do it again, but I’m glad for every step of the way.

There is a scripture that says, “all things work together for good.” I have found that to be true. Even the mistakes, challenges and shortcomings have shaped my character and have worked together for good. I have learned and appreciated that the hardest things are the best things and the best things are the hardest things.