Deanna Castellini, Co-Owner, Cincinnati Reds; Founder,


DEANNA PHOTODeanna founded in 2007 with partner Cris Collinsworth to engage the next generation in service to their communities and world. Deanna created the strategy, leading development, and works full-time to grow UGIVE from concept to a national movement. Previously, Deanna was a banker at Morgan Stanley in New York and London where she was engaged in Strategic Planning. Deanna began her charitable work in Mission Hill in Boston as a student at Harvard, where she graduated with Honors in Economics. Deanna is currently the Senior Advisor to the Chairman at Changing Our World, a Philanthropic Consulting Services Firm. She also serves on charitable boards ranging from athlete foundations to the Jefferson Awards and has chaired numerous Galas, fundraisers, and community initiatives, including those involving her family-owned Cincinnati Reds. Via UGIVE, students across America are volunteering daily for all types of causes, and their service is tracked via their personal online verified service resumes that they can use for college applications and scholarships. UGIVE engages athletes across sports to motivate and inspire students to serve.


Key Takeaways:

Deanna Castellini Takeaway

How athletics can shape leaders and drive change

  • Athletics taught me to be resilient
  • Athletes have a certain mental toughness and discipline that really comes in handy during times of crisis
  • Sports can be used as a catalyst for these conversations about building a network of people that relate to each other in different ways and add value to the community. It’s all about relationships and building trust, rather than creating protectionist visions that are unsustainable.

Advice for women in the industry

  • In the education sphere, knowledge is power
  • My kids see me putting my time towards something purposeful and they appreciate women as a result
  • You have to be comfortable in a lot of different environments

LifeChat with Deanna Castellini:

How do you think the athletic background prepared you for success?

After I finished my undergraduate degree at Harvard, I worked in internal mergers and acquisitions as well as strategic planning at Morgan Stanley. Overcoming the bias against women was the first problem I encountered, but I was fortunately able to deal with it because of my experiences in sports at Harvard.  I was a gymnast turned cheerleader (since Harvard didn’t have a gymnastics team). Athletics taught me to be resilient, when I faced the challenges of perception by others of being a cheerleader athlete, and to work in a team setting, supporting all the different sports teams or as an unofficial liaison between the athletics department and student athletes when issues arose.

When I joined Morgan Stanley, I had assumed that I would face the same challenges of perception as at Harvard; people looked at a blonde girl on Wall Street and made the same assumption that many people made when they looked at me as a cheerleader.

I took a chance and worked in a department that I really shouldn’t have been in yet, because most of the other employees there were business school graduates. Even though I was the youngest, I acted older and looked older, and fought the inherent bias that others held against me. I ended up being successful.

How do you think athletics prepare others for today’s tough work environment?

I started the first analyst program in the department at Morgan Stanley.  I hired twelve young adults.  Since Morgan Stanley worked as a meritocracy, I had the opportunity to hire some unique talent and ironically, most of them were former athletes. I started to take notice of the qualities that the former athletes brought into the workplace. When the going got tough, I could count on them. When we had to pull all-nighters, they never had a problem with that because they were the ones running in the rain and rallying their teams together. Athletes have a certain mental toughness and discipline that really comes in handy during times of crisis.

It’s easy for team decisions and judgment calls to become driven by passion plays rather than strong business principles. How do you bring the business perspective in, as co-owner of the Cincinnati Reds?

My angle has really been on the community engagement side of things, which spills into marketing as well as corporate social responsibility.  For years, teams would buy tables at dinner events, but not really make an organized effort towards any one cause. At Cincinnati Reds, we get at least 400 requests a week, and you can’t say yes to everything so you have to tap into your true mission and evaluate your impact in giving back to the community.

When our family took over the Reds Community Fund in 2006, we did a lot of great things but it was kind of disjointed. We brought everything in-house, and decided to make our partnerships with the community about baseball. That’s our business – we weren’t just going to build baseball fields. We were also going to train the coaches and fund long term projects.

We’ve ramped that up to building an urban academy in Cincinnati for all children, not just the kids who are the most gifted athletes. We’re working in the Dominican Republic and Mexico to make sure that kids are educated all the way through high school, whether or not they’re superstars. This is business, too. There will be a return on this investment because these kids will become baseball stars, baseball fans, or people who will buy tickets. The community gets more involved, but the return isn’t just in community dollars.

You can get flak in the short run for doing something like this, but in the long run you’re making a greater impact, giving ten times more than money, and creating change.

Business sustainability is all about societal stewardship, leveraging you and the organization’s talent for societal good and building a business case behind it. Do you think that you’ve been able to duplicate this in your other projects, as well?

I want to combine all of my experiences and try to do some good with it by maximizing the dollars out there that are not been maximized effectively. I enjoy teaching other groups what I’ve learned along the way, and want to make these differences across the board.

I started UGIVE.ORG with my partner, Cris Collinsworth. UGIVE.ORG is a non-profit organization on a mission to catalyze, excite and empower the next generation of volunteers. We really believe that students should find their niche as far as charitable causes are concerned, so we seek to provide students with meaningful opportunities to serve those causes. UGIVE has a free online accounting system that schools can use to calculate the hours of service that students do.

We spent millions of dollars building UGIVE, and on Muhammad Ali’s seventieth birthday we gifted UGIVE to the Muhammad Ali Center. Now, they’re going to run with that, make it more global, and use the system to run their peace and service initiatives. Technology, as far as I see it, should be for the betterment of the world. Free is the way to go.

Now, I’m collaborating with one of the best philanthropic consulting firms, called Changing Our World. They’re creating a sports and entertainment arm of their business, which is great because unlike so many others in the sport industry, their only agenda is to make what they’re doing more efficient for their business and the community. In the education sphere, knowledge is power. There are so many corporate leaders and philanthropists going out and starting their own causes.

Sports can be used as a catalyst for these conversations about building a network of people that relate to each other in different ways and add value to the community. It’s a long-term thing. It’s all about relationships and building trust, rather than creating protectionist visions that are unsustainable.

So you’re traveling the world, growing UGIVE; sitting on various boards; working with Changing Our World; and being a mom to two sons. How do you keep it all integrated and in balance?

Well, just like any other occupation, mothering requires you to be well organized. That is definitely step one. Being organized minimizes the stress of juggling these different things. I have to plan my schedule around my children’s’ big dates like the school play. I would never want to miss something super important because I’m on a trip to London or South Africa or wherever.

Another important thing is to take everything one step at a time. I believe in involving my kids in my work. I talk to them like they’re adults. For example, I take them to New York and California with me, as well as to schools with UGIVE, so they understand what I do as best as they can at their age. They’re in tune, they appreciate me, and they recognize that mom works.

One of the best day of my life was when we were grocery shopping in Kroger and my son Alex was in kindergarten. There were two teenage girls wearing UGIVE shirts, and Alex walks right up to them and says “Hi! UGIVE, huh? My mom works there!” I like that my kids say that I work there, not that I started it.

My kids see me putting my time towards something purposeful and they appreciate women as a result. They expect women to do great things. I think it’s important for our sons to see that and not to see the family from the 1950’s where the father brings home the bacon and the mother does what he says. I can be on Wall Street one day, the White House the next, and scrubbing cafeteria floors because my kids threw popcorn on the floor during chess club the next day. Being comfortable and confident in each of these places is key – you have to be comfortable in a lot of different environments. Maybe this has to do with sports, too.

You’re very entrepreneurial, clearly, as well as fearless. What advice would you give the twenty-year-old Deanna?

Have no fear, and don’t let anyone hold you back. I hope you will be doing something completely different in five years, working with new people and setting new goals.


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