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Brett Diamond, 33

DeAngelis Diamond, Chief Administration Officer and Principal

  • By Mark Gordon
  • | 5:00 a.m. October 14, 2022
  • | 2 Free Articles Remaining!
  • Class of 2022
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Brett Diamond’s LinkedIn résumé says he’s worked at Naples-based DeAngelis Diamond, one of the largest construction firms in the region, for eight years. He started in 2014, overseeing technology.

But his tenure at the firm, co-founded by his father, David Diamond in 1996, really dates back two decades, to when he was a summer intern at 13 years old. Today Diamond is a principal and chief administrative officer at the firm, a role that includes overseeing IT, data and HR. DeAngelis Diamond posted $365 million in revenue in 2022, landing it at No. 3 on the Business Observer’s 2022 Top 50 ranking of the largest contractors in the region.

One constant in Diamond’s career at the firm, going back to when he was a teenager, is his desire to always be learning and searching for better, quicker and more efficient ways to do things. That ranges from advances in building technology to hiring software to new and enhanced benefits.

For all those areas, Diamond has partially leaned on other businesses he’s started with his dad, such as Venture X Naples. That one, a private membership office space venture, dipped into co-working space long before it was cool. Diamond has also sat on customer advisory boards for Procore, a construction management software service company; cloud computing firm Box; and DocuSign. At each stop Diamond analyzed and took back some of the best parts of each business.

One big takeaway led from those experiences led to the creation of Team Beni at DeAngelis Diamond in summer 2020. Named for benefits, the 12-person inter-departmental team looked at adding benefits and improving existing ones, all with eye toward employee recruitment and retention.

Outside the core work of the company, Diamond also relishes the leader part of his leadership role. That came through in the early days after Hurricane Ian, when the firm went into crisis management mode to check on its team, vendors, clients and projects. The company has nearly 200 employees in total, and about 100 in Southwest Florida.

In a video posted to LinkedIn Oct. 3, Diamond gave a shout out to employees and department heads who headed to the office, boots on ready to work, as soon as it was safe. Once there, they found Diamond and firm co-founder Jeff DeAngelis, already at work to check on employees they hadn’t heard from and other tasks. (David Diamond remains CEO of the firm, and was in Phoenix prior to and during Ian.)

“That’s when you see the best in leaders,” Diamond says in the video, “when people show up without asking them, and are ready for action, at a time where their homes might be having issues and they have family to take care of.”

— Mark Gordon

• City of Residence: Naples

• Marital Status/Children: Married with three children   • Alma Mater/Degree: FGCU   • What community group or organization are you most involved with? FGCU Foundation Board   • Are you working from the company office, home office or hybrid? Home Office and HQ in Naples   • What's the weirdest job you've ever had? Or the weirdest task you've ever been assigned? I was a janitor in college. My landlord hired me, he knew I had to pay rent somehow.    • What's your top tip for being productive? Set challenging but realistic goals for each day. Don't end the day without each of those goals being accomplished.   • If you could have a side hustle, what would it be? Day trading   • What's your favorite off-hours activity? Supporting my kids in their extracurricular activities.   • What's the most significant item on your life bucket list — and what's keeping you from completing it? Road trip across the country. Waiting for children to be older (six, four and one)   • What's your favorite podcast? All-In   • At what percentage on your phone do you start to get Low Battery Anxiety? 1%   • What are the top three apps used on your smartphone? TradingView, YouTube, Twitter   • What books are you reading now? I mostly listen to podcast. All-in & Lex Fridman.   • What's your go-to music genre, band or act to be inspired? Country - Morgan Wallen

 •Who would play you in the movie of your life? John Krasinski

• Where is your happy place? Gym   • Describe yourself in three words: Determined, Competitive, Authentic   • Who is your mentor for your career and why? My dad, David Diamond. He's insanely intelligent, driven and passionate about what he does and what he wants. It's impossible to not strive to do the same thing.   • What are the biggest lessons you have learned from your mentor? Be passionate, authentic, and knowledgeable. If you're going to be successful in any endeavor, you need to love what you do. That's step one. The rest can be learned. Whatever business you run, be authentic to the client and your team. Strive to be more knowledgeable than your competitor. Continue to learn, adapt, and innovate your brand to lead the industry and where it's heading. Lastly, always hire people smarter than yourself, especially in areas you are naturally weaker at. You will eventually hit a growth wall if you're the smartest in the room. Put aside the pride, build a strong team, and push forward.


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