Conor Caloia, Big Top Baseball/Madison Pro Soccer

IB’s Professional of the Week is the premier way to meet Dane County’s professionals. This week features Conor Caloia, chief operating officer/partner, Big Top Baseball/Madison Pro Soccer.

What are the most challenging and rewarding aspects of your job and why?

We are in a time of rapid growth across the state as we expand into soccer in Madison, and build a new stadium and launch a soccer team in the Green Bay market next year. Furthermore, we have laid the groundwork to expand into the Milwaukee market in Waukesha in 2020. The most challenging part is making sure we have the right people in place to grow our current businesses while launching new markets successfully. We are fortunate to have a creative, hard-working, and dedicated leadership team and staff that is the key to our expansion efforts.

While the growth creates challenges, it is undoubtedly the most rewarding aspect of my job. Our venues attracted nearly 600,000 guests in 2018 and we hope to be closer to 1 million guests per year by 2021. Additionally, I take a great deal of pride in the jobs we have created and the experience we provide to our great staff of 40 full-time employees and 700 seasonal employees.

Who do you look up to or admire in business and why?

Locally, I admire the work ethic and business acumen of Dave Fritz, CEO of Tricor Insurance. I have never met anyone who works harder and pays such great attention to detail. Dave has had success in a variety of businesses ranging from insurance to beer to real estate and farming. He has led the growth of his small family insurance agency to 28 locations across the state. I admire the businesses he has built, but I have a greater appreciation for how he takes care of friends and customers. The recent flooding significantly impacted us and Dave was one of the first ones there to help lead the restoration and recovery efforts.

What has been the high point of your career so far?

Our efforts of the past few years culminated in several major developments in 2018. First off, we finalized a 10-year lease extension for Breese Stevens Field that will see $2.5 million in improvements to the facility and allow us to bring professional soccer to Madison in 2019. We also reached an agreement for an $11 million new stadium in Ashwaubenon near Lambeau Field. The new facility will host baseball, soccer, and concerts. Finally, we finalized a contract with the City of Waukesha for a new $12 million facility to also host baseball, soccer, and community events. I hope the high point of my career is yet to come, but 2018 has brought three major agreements that set the path of our company for the near future.

Thinking back on your career, what advice would you give your 21-year-old self?

Your career is going to being long, so don’t feel that you need to accomplish everything with your first job or even in the first five years of your career. I think being ambitious and lacking patience has served me well in my career, but it also caused me to look past other opportunities that may have come about had I not been so focused on my next opportunity. The best thing that has happened in my career was making mistakes and learning lifelong business lessons at an early age. When I was 25, I entered into a bad business partnership. It was painful at the time, but it is one of the best things that has happened in my career. Early in your career you are going to make mistakes. It is important to learn from them and be better moving forward.



What would you say are the best things about living and working in Dane County?

Madison is a great place to raise a family, making it attractive to employers and potential employees. The overall balance allows for a high quality of life. We are fortunate to have a vibrant community with so many events and entertainment offerings, beautiful lakes with a great local parks system, and a world-class university. There are a lot of reasons for people to come to Madison and our great community is what gets people to stay here.

Do you have any secret talents or abilities that people would be surprised to discover?

Unfortunately, there are many areas I wish I were more talented than I actually am. With that being said, I recently bowled a 223 after not having gone bowling in seven years. I am not sure if I will ever repeat that, but maybe I am secretly a competitive bowler.

What are your guilty pleasures?

I am a craft beer enthusiast and enjoy breweries from across the state and around the country. I started and sold a small business that worked directly with growing craft breweries and startups. I enjoy watching the industry evolve and following consumer trends. Whenever I travel, I make a point to sample local breweries and offerings.

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