"No matter what job you're doing or where you're going, you always want to be the best at your current role. I never imagined that I'd be in the sports industry, let alone the President of an NHL Hockey Team. I never imagined that I'd be at Goldman Sachs. When I was in the Army I just worked really hard, and then identified that my next step would be getting into the best grad school, and then I just focused on that. You just have to have this balance of short term and long term planning." - Matthew Caldwell

Matthew Caldwell is the President and CEO of the Florida Panthers and Sunrise Sports & Entertainment. Matthew started out at West Point, after which he served in the U.S. Army for five years, conducting combat operations in Iraq and peacekeeping operations in Kosovo. Matthew worked as a Vice President at Goldman Sachs in their Investment Management Division, and then transitioned to Chief Operating Officer for the Panthers before being elevated to President and CEO. Matthew holds a JD/MBA from Northwestern University School of Law and the Kellogg School of Management

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Selected Resources

• A guy that I most recently have really started following and has been Simon Sinek. About six months ago I found him, and he's done so much research and it's not specific to sports, or finance, or technology. His TED talk is: Start With Why - it's why great leaders inspire people to take action. It's a simple kind of concept but it's all about understanding why you exist. Whether you're working at Apple or wherever you have to figure out why... your purpose... your vision for the future. These are things we kind of did in the military but it's so important. A company like Apple, they exist because they're always challenging the status quo.  The book is fascinating because he covers sports teams, Martin Luther King, Google, Apple... it's very interesting.
• He also has another book - Leaders Eat Last. I think people in the military will appreciate it.
• iv'e gotten into sports books - culture and how people operate is so important to them. I read recently the Real Madrid Way - its the most valuable sports franchise out there. Steven Mandis is a Goldman alum too, and i reached out to him and we talked for an hour about why Real Madrid was so valuable and what they've done in the community.

Show Notes

Please note that I type these notes during the interview so there are likely to be misspellings, grammatical errors, and misquotes. This is not meant to be a verbatim account of our conversation, but a VERY basic text transcript of our discussion.

• How did you approach the decision to leave the Army?
  • It was the toughest decision I've ever had professionally. I went back and forth on it a bunch of times. I was in the Army for five years - the first three I was deployed, in Iraq, Kosovo, or a build up for that. It was very high tempo. Ironically, when I was deployed, I actually really enjoyed it and felt like I was making a difference and serviging a highe rpurpose. When I got back, I was stablized for a year, the garrison lifesytle at my base in Germany. I went back and forth for a year but realized I enjoyed teh Army most during dpeloyments, and that's not all the time. I didn't know if I wanted to go special ops and sustain that op tempo for long-term. Ultimatley I decided I wanted other things besides the Army. I didn't think I could deploy every year even though I enjoyed it. I thought graduate school was a natural next step and then se
  • How did you decide on a JD / MBA program?
    • I always liked business and reading the Wall Street Journal and hearing what companies are doign and reading Good to Great. I thought an MBA was very suitable in opening me up to different industries. When I started researchign schools Noerthwestern was my top pick - I love the Chicago area and their culture. They ahve this very integrated, but also very exciting JD/MBA program that was in three years. I thought I'd get a taste of both business and law. I applied to a bunch of buisness schools and thought if I could also get a law degree it'd make me better at busienss or maybe I'd like law instead. Most programs are around four years and it's a lot of money. For me it was a good fit.
    • For advice for other veterans, it really did work out for myself. I had all this leadership experience, I had lived overseas and had a good world view. So I had a good view of what was out there - for me to come home, as much as I had an interest in business I had no idea if I would be a consultant, a lawyer, finance - I was all over the map. For me it was a three year reset. And the networking aspect was most important. If you go to West Point for four years and then five years in the army, that's nine years of uyour life (one third of your life at that point) where you're just with a mlitary segment. It's a secdluded world. To get out and meet people from different backgrounds, hear about what they did and what they did in the workforce, that experience was very eye opening to me. I learned what they did and they were a great resource. It was the perfect transition point for me.
    • Some of my friends got work experience before grad school and I can see the value of that. When people were talking about a case study, i didn't have any context for what they were talking about.
    • What lead you to Goldman Sachs?
      • Most people in business school go to all the networking events, take classes, talk to people and build from the bottom up. I want to be in Private Equity, in the MErgers & Acquisition world. They identify an industry and then start interviewing in certain geographic areas. I looked at I knew I wanted to go to business and enjoyed those classes and then - what company do I want to be most associated with. I did an exhaustive search and talked to consulting companies, and General Electirc, Proctor and Gamble, etc, but I felt like I connected with the banks. I like JP Morgan & Chase, Goldman, etc - I connected with the people at Goldman. They were diverse, hardworking, and wanted to be in an environment like that.
      • There were three areas: the trading side of the house, i enjoyed that mentality but didn't know long term. Investment banking house where working on big deals with major institutions. But ultimately the investment management division was a good balance between working with big institutions on how to invest their capital but also resonate with me long term.
      • There were a few West Point guys who mentored me.
      • For someone on active duty, how would you explain the work you did at Goldman Sachs?
        • It is a great firm - over many generations they've produced great people who have done great things for the country.
        • My every day life there I worked on a team with about six individuals managing thirty or so accounts. Big families, foundations, non-profit, another company's assets, etc. We were the intermediary between the client - what are their needs, what are they trying to do - and then sit with all the experts at the firm (in research, or investing in Europe, or Latin America, etc). We'd be the intermediary between them and the resources at Goldman. A lot of my job was listening to my clients, hearing their needs, running around and talking to different departments and then making recommendations.
        • What advice do you have for a veteran aspiring to work at Goldman Sachs?
          • The banks or any firms on Wall Street generally like military. They appreciate the tenacity, the hardwork, the comraderie - the characteristics of many service men and women. You put the organization first. The company is more important than the individual. That's not common everywhere. A place like Goldman really values that. It is a tough firm to get into - they usually only hire right out of college or an MBA or other graduate program. They value talent and intelligence and very diverse backgrounds.
          • If you have an interesting story and they think you can add a lot of value at the firm, they know they can teach you all the finance technique. It's just a matter of hustling to get in front of the right people. I've gone through a job search a lot of times - it's a matter of reading and talking to the right person. Sometimes you do 20 coffee chats and yuo don't feel like you're making any progress, and then the 21st meeting and it's the perfect meeting. but if you didn't go through all the reps before that you don't know how it would have worked out.
          • I was at school in Chicago and was interested in going to New York. And I wasn't able to get a time to meet with anyone else. I sat at Starbucks all day emailing people and calling them and I figured since I was in NY I might as well try to meet with people. And that got me in touch with someone who was at Credit Suisse who was West Point, he had a few minutes available and I sat down with him. I was open and honest that Goldman was my first choice,; and he introduced me to someone at Goldman. 30 interviews later I got a job there.
          • What lead you to make the transition to the Florida Panthers?
            • I was at Goldman and one of the unique aspects of their culture is that the junior people are the ones who are encouraged to get out there and kick up new business. Typically in firms more senior partners are trying to drive new client relationships. At Goldman they send out their more junior folks. So I was out there talking to institutions and big family offices trying to get them to invest at Goldman. So I was out there hussling and same thing as I did whe ntrying to get my first job. I started a relationship with another West Point grad, Vincent Viola. he ended up becoming a client at Goldman, and was great at investing his capital. We built this great report with him over time and he took a liking to me as a younger West Pointer who got his start on Wall Street. It was very familiar with his background. He went trading and came from Brooklyn (I'm from Staten Island). After a few years he asked me to come and join his family office. So I jumped at the opportunity. As much as I loved Goldman I thought it was something I couldn't' pass it up.
            • I was dreading going to the guy who hired me and probably got ten seconds into my pitch and he said, 'I would love for you to build a career here, but you gotta jump on this.' So i started working directly for Vinnie. He had purchased the Florida Panthers hockey team. He always wanted to get into sports - it's hockey in South Florida, which is tough. We knew there would be a big challenge, he said, I'm a very hands on operator and could use someone I could trust.
            • I signed up for it, and moved down to South Florida. I live in Miami, started off being an ownership representative giving him advice on how to improve the franchise. how to sell season tickets and get the stadium packed. They ended up giving me the COO role as a permanent role. As the franchise turned around 1.5 years later, and he named me the CEO and President.
            • How would you explain your role as CEO?
              • I was a huge sports fan of every sport. There's actually another West Point graduate, Eric Joyce, who was an Assistant Captain for the West Point hockey team. Eric was his guy to help out on the hockey side. And he's done a great job and is the assistant GM. Initially I focused more on the business side - it was more selling the team and keeping the budget straight and sending reports to people about our marketing plan and sales plan. everything that happens off the ice.
              • Right now there's different periods where things change dramatically. We're in the office season so things aren't top of mind for people. However, for the business side of the operation its an important time to knock out some long-term projects. A big thing we're doing right now is formalizing our marketing plan, getting feedback from all the different departments on what will be our slogan this year, how to attract more fans, how to get a big excitement around opening night. It comes on October 7 and so we hit the pause button and think about our identify, our team and how to tell our story to our fan base.
              • We're also very active in our grassroots - sports aren't front of mind - we go door-to-door and go to local boys and girls club events and anything to support our team and show our presence. There's more of an emotional presence between the team and the community
              • After labor day the whole coaching staff and players and hockey side comes and then its about supporting the training camp. And it's ver intense and we want to make sure the fans have a great experience. Visiting suites and clubs and showing them a great time in the stands.
              • Additionally, I'm President of Sunrise Sports & Entertainment that operates  - we got Bruno Mars and John Mayer coming through. All the ushers, all the ticket tapes, all the people who run food and beverages. We want to make sure they have a great experience.
              • What advice do you have for a veteran seeking a career in the sports industry?
                • I don't know if it differs much from other industries. a lot of companies value how interested you are in something, and if someone is leaving the military in six months you need to start reaching out to sports teams or anyone who has any connection there. Go on LinkedIn or Facebook see who you know - give them a call. Start hearing things. See if that sounds interesting. Do you know anyone in the NY area? Get introduced and start having that conversation. Any industry will respect a veteran reaching out. It's not that you have to prove anything. They won't hire you because of your specific job in the military they just want to know you did a great job. No matter what job you're doing or where you're going, you want to be the best at your current role. You can fall into the mistake of coasting or thinking of what you'll do next. The problem is you never know where your career will take you, and it's important for recommendations and when you want to tell stories in interviews and why you did a great job in the current job where you are. Just worked really hard and identified my next step and just focused on that. You gotta have a balance of short term and long term. Research industries, do a great job.
                • What resources - books, programs, seminars, conferences - have helped you in your civilian career that you would recommend to other veterans?
                  • A guy that I most recently have really started following and has been Simon Sinek. About six months ago I found him, and he's done so much research and it's not specific to sports, or finance, or technology. His TED talk is: Start With Why - it's why great leaders inspire people to take action. It's a simple kind of concept but it's all about understanding why you exist. Whether you're working at Apple or wherever you have to figure out why... your purpose... your vision for the future. These are things we kind of did in the military but it's so important. A company like Apple, they exist because they're always challenging the status quo.  The book is fascinating because he covers sports teams, Martin Luther King, Google, Apple... it's very interesting.
                  • He also has another book - Leaders Eat Last. I think people in the military will appreciate it.
                  • iv'e gotten into sports books - culture and how people operate is so important to them. I read recently the Real Madrid Way - its the most valuable sports franchise out there. Steven Mandis is a Goldman alum too, and i reached out to him and we talked for an hour about why Real Madrid was so valuable and what they've done in the community.
                  • Final words of wisdom?
                    • Taking a risk. Quick anecdote, when I was in business school I was able to sit with the student admissions team. I sat in the room and heard right from the Director of Admissions who was letting people into Kellogg. And they said they see resumes from veterans and have no idea what it says. As much as we try to dumb it down and not use acronyms, it still sounds foreign to people. It's difficult to pull info out of veterans. We're trained to always put the organization first and focusing on the unit. We're trained not to self promote. It's a tough thing to do - you've gotta spread the needle about promoting yourself and clal someone and explain why they should take your call or why they should get on the phone with you.
                    • As a veteran you don't want to ask for favors - you want to be rewarded for performance without pounding your chest. It's this difficult balance. IF you feel like you're self promoting you probably arne't- it just isn't. if you don't do it, no one will.