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Co-Founders, Massimino Development

Could you share more about how you two met?
Ben and I met our sophomore year of college. He was the ATO Powderpuff football coach, and I was a Chi Omega. I wasn’t playing football at first but kept hearing all my sorority sisters talking about the super cute coach. Finally, I had to check him out for myself and showed up to play. Coach Ben wouldn’t put me in. He said it was because he was afraid I’d get hurt. I kind of think he liked me on the sidelines near him! 

We didn’t meet again until a huge snow storm rolled into Boulder, and school was canceled for the first time in years. We were both on the Hill that night. My friends saw Ben across the street and brought him over. I vividly remember sitting in the crowded booth with friends and hitting it off with him, dancing the night away, walking home and then the kiss out front of the Chi O house. Little did I know I had a lot of friends watching from the window who immediately declared my love for Ben. We’re one of those couples who knew fairly quickly we were meant to be together. 

Do you have any advice for couples who work together or aspire to work together?
My biggest advice for couples working together is to realize it is not for everyone and know what you are signing up for! Second, do not blame your spouse for failures. Lastly, know when to shut off work and focus on being a couple.

We do try to find ways to do two things at once; for example, we have a weekly meeting in our outdoor office, which means hiking any of the many trails around Boulder and working through our to-do list, talking about our new ideas and organizing the workload between the two of us. 

We know each other’s limits and recognize they can change. For us, it was a juggle and struggle when I started to work full time. I was frustrated managing everything for the household while trying to learn the business. It also took a bit for Ben to adjust to me being involved in the business; he was used to doing everything himself. A couple of years later, we both have our roles in the development company, and we share all of the responsibilities in our household (making lunches, driving carpools, managing homework and a house full of teenagers) otherwise there’s no way either of us can do what we do. 

My other piece of advice is don’t blame your spouse for failures. As with any partnership, there will be a losing investment or poor business decision. We’ve had our fair share. The one that most significantly impacted us was opening a franchise sandwich shop that epically failed and nearly pushed us to bankruptcy. However, this pushed us to dive in head first and focus solely on real estate development. We sold everything and invested everything into our business. Now, we are seeing the benefits of working together as our projects are taking off. 

What are some of your favorite ��������Ƶ memories?
There were so many memories during our four years at ��������Ƶ, its’s hard to just pick one or two. Some of our fondest memories at ��������Ƶ are going to the football games: meeting up with friends before a game, walking through campus—usually stopping by Farrand Field, which was a buzz with students—and then heading to the stadium in what seemed like a flood of black and gold. 

We also cherish the daily memories of life at ��������Ƶ: walking through campus, hearing the band practicing at Farrand Field, the bright blue sky and the sun drawing everyone out to enjoy Boulder’s amazing Flatirons. I loved trail runs at Chautauqua Park, and Ben's favorite memories were bowling for beers at The Connection or heading to the Walrus to play pool. 

We’re proud to say that our oldest son will be attending ��������Ƶ and the Pre-Business program next year. As he starts his new adventure as a Buff, we will continue revel in ours! Go Buffs!

Why did you decide to come to Leeds? 
I (Olivia) came to Leeds because it offered a great foundation of business whether I started my own company or worked for someone else. 

Could you share an experience (or two) that was particularity memorable at Leeds? 
One of my most memorable experiences at Leeds was working on business plans in an entrepreneurship class. It was a fun project. My business was in the travel industry offering custom itineraries and concierge services. I really enjoyed the process and building my dream vacation. A few years ago, I was able to take my family to a few destinations I included in this project. I also really enjoyed my finance classes; they were challenging for me, and my peers really made the experience enjoyable. 

Any particular professors or mentors that influenced you while you were at Leeds? 
My  peers were some of the most influential people I met at Leeds, and it's been a pleasure to see many of them flourish professionally [since college]. 

Where has life taken you since you graduated Leeds? 
After graduating, I thought I wanted to purchase a small boutique on Pearl Street. It wasn't a good fit for me, and  I landed an administrative position with a start up company and worked there for little over a year. I married my college sweetheart, Ben Massimino, also a ��������Ƶ grad. We started our family very early and moved to Park City, Utah, while we were expecting our first child. We lived in Park City for 17 years and raised three children.
    
While in Park City, I started a property management company that offered an array of concierge services to high-net-worth home owners. It was fun, but eventually, it was too demanding for a growing young family, so I sold the business. While I managed being a “mom,” I would also help my husband with new business ventures he was starting. In 2015, I injured my foot, which put a huge damper on my lifestyle in Park City, and I had way too much time on my hands. We had a great home office that Ben would use, and I would ask Ben a million questions every day, trying to figure out how I could be more involved. Eventually, I moved into the office with a desk directly across from Ben's. I loved it, and thankfully, my husband and business partner is incredibly patient and has been my biggest mentor. I have learned a tremendous amount over the last five years! 
In 2016, we pivoted the focus of our development company to the Colorado Front Range. Our development pipeline grew significantly, and we made the decision to move back to Boulder in 2017. We rebranded our company to Massimino Development. Right now we have two developments under construction, three developments on track to break ground in 2020, and we're expanding our business to include hotel development. 

What is one piece of advice/best practice that has stuck with you throughout your career? 
I try my best to live by three things professionally: stay humble, always learn and have tenacity. For me stay humble is remembering who and I where I came from and how I've gotten here. I believe our failures, challenges and struggles shape us just as much as our successes do. Believe in yourself and surround yourself with a team and hopefully a partner that is a positive influence for you personally and professionally. Always learn this is something I preach to my children every day, especially my senior in high school. My education continues on a daily basis, and I am always asking questions. Lastly, have tenacity.  

Is there anything else you would like to share? 
Since moving back to Boulder, we’ve really enjoyed reconnecting with our ��������Ƶ Alumni, attending the ��������Ƶ football games and getting more involved at ��������Ƶ in general. We really enjoy sharing our perspective and experience with the MBA Real Estate class taught by Stephen Billings.

To nominate yourself or a fellow Leeds alumnus or alumna to be in an upcoming alumni newsletter, 

February 2020