For years, Jim Nagle drove a bus for the Chicago Transit Authority before opening a law office in the 1990s. Ten years later, he launched Pima Properties, owning and operating more than 1 million square feet of commercial and multifamily real estate.
In 2013, he and his wife Tely acquired the historic Drake Oak Brook hotel, which had closed following a Ponzi-scheme collapse, and Jim transitioned into yet another industry. The property underwent a major renovation in 2019 and joined Marriott's Autograph Collection.
Today, Jim Nagle personally reviews more than 30 education scholarship applications from the children and grandchildren of the hotel's team, and ensured that every applicant for this academic year received a scholarship.
What first got you into hospitality?
The Drake was part of my family long before it was my business. I grew up in Elmhurst, and The Drake Oak Brook was woven through my whole family’s life. My grandfather brought the whole family here for Easter Sunday, my cousins were married here, and I kept coming back over the years for Bar Association functions, high school reunions, even memorial lunches. Generations of my family’s memories live in this building. When it fell into disrepair and collapsed in a Ponzi scheme, rescuing the hotel wasn’t only a business decision, it was personal for me—so my wife Tely and I jumped right in and began a two-year renovation that preserved the hotel’s historic character while restoring its grandeur.
Who were some of your mentors when you were getting started?
I have had many mentors throughout both my legal career and in real estate. But the man who changed my whole direction was a real estate investor named Slobodan Pavlovic, who came to Chicago as an immigrant and built a career acquiring and restoring run-down commercial properties. Watching how he created value out of overlooked buildings sparked my interest in real estate investing and ultimately led me to step away from my legal career in 2008 to fully pursue this new path. Then, when Tely and I acquired The Drake Oak Brook, and with no hospitality background of my own, my mentors became the people right beside us—the crew we built from day one, who quickly became family. Their talents are truly what made The Drake’s revival possible.
What were some of the most important lessons you learned early in your career?
Before I entered the hospitality world, I drove a CTA bus through the streets of Chicago, which taught me a great deal about how to treat people—everybody who steps aboard deserves the same respect. I've carried that with me ever since, and it's still a key principle behind how we run The Drake, which is rooted in teamwork and a people-first mindset. Another important lesson I’ve learned is to tune out the word “no.” Throughout my career and especially through the process of transforming this hotel, I lost count of how many people warned me it would never work or told me flat out not to try. I’m grateful I never listened.
What is the biggest professional challenge you’ve faced in your career? How did you overcome it?
Saving The Drake Oak Brook was certainly the most challenging, but also the most rewarding, part of my career. When we took it on in 2013, after it had gone dormant in the Ponzi scheme collapse, I was coming off the recession with very little capital and no experience running a hotel. The building was in extreme disrepair and needed extensive renovations, and we didn’t have the funds for an outside contractor. So instead, we retrained our loyal hotel staff as a construction crew, and Tely and I worked alongside them on drywalling, painting, decorating, all of it—and rebuilt the place over the course of two years.
What was one of your proudest professional accomplishments? Why is it meaningful to you?
One of the first things that comes to mind is our Condé Nast Traveler recognition. Being named one of the top 50 hotels in the world was such an honor and validated everything our team has poured into the property. But what I’m proudest of is how we look after our team and their families. We have an annual scholarship program for the children and grandchildren of our staff, and reviewing their applications is one of the parts of my job I look forward to most. Last January, we awarded one hundred thousand dollars so that every single applicant, more than 30 students, received a scholarship. During COVID, when hotels everywhere were cutting people, we were able to avoid layoffs entirely—making sure not a single person lost their job. That means more to me than any award.
What brought you to your current position?
It's been an unconventional path—as I mentioned, I even spent some time driving a CTA bus along the way. I trained as a trial attorney and represented hundreds of businesses and individuals in state and federal courts, and after authoring the constitution for Bosnia, I transitioned into real estate development in the early 2000s. Over the years I developed just about every asset class there is, including multifamily, retail, office and industrial. So when we purchased The Drake in 2013, although I didn’t have hospitality experience, I did have the development and construction experience the project required. Today I'm the owner and managing partner of the Drake Oak Brook, a Marriott Autograph Collection hotel, and I run my own construction firm, which has handled every one of The Drake's renovations. None of it followed a straight line, but it all prepared me for The Drake, which has become the most meaningful work I've done.
What is the best part of your job?
The best part is getting to do all of it alongside my wife, Tely and our family. We built The Drake Oak Brook together, and we have so much fun sharing both the work and the wins with one another. Every morning, Tely and I make our rounds of the property, saying good morning to guests and catching up with the team, and it's a part of the day we always look forward to. I'm especially proud that women lead so much of what happens here—alongside Tely, we recently welcomed the hotel’s first female general manager in more than a century, and championing women in hospitality has always been a real focus for us. Then there’s the creativity. We get to dream up experiences for our guests that you'd never get away with anywhere else, like our $1,893 version of the hotel's historic Bookbinder Soup and then watch the team run with them. Above all, I love always working to make The Drake better, as both an anchor for the Oak Brook community and a welcoming place for visitors.
What do you hope to be doing five years from now?
We’re continuing to develop The Drake Oak Brook and have many exciting things planned for the coming years, but the venture I’m most excited about started with a single hire. Twelve years ago, a young man named Tekste Gebreslasse walked into the Drake from a small village in Ethiopia looking for work. His middle name, Haile, honors Emperor Haile Selassie—who stayed at the original Drake in Chicago during World War II—so the whole thing comes full circle. Today we’re partners, building a hospitality venture that bridges the Midwest and East Africa. We've now completed three Drake Luxury Hotel deals on the continent—with the latest being Drake Djibouti—and we have four more in the works. Five years from now, I hope to be doing exactly what I’m doing today: Saving beautiful places, betting on good people, and bringing the next generation along with me.