The Challenge of No Longer Having Tennis & What It’s Like to Navigate Jobs in Finance


This article covers the perspectives of two former University of Chicago Tennis Players, nine years apart, who built their careers in finance. We cover their respective moves to New York, their experiences making the transition, and advice they would give to student-athletes.

Deepak Sabada (’15) played tennis at the University of Chicago, where he was an All-American and earned UAA (University Athletic Association) All-Academic honors. After graduation, he pursued Investment Banking in New York for two years before returning to Chicago to start his current career in private equity. In this interview, Deepak talks about the challenges of leaving tennis, the importance of small details when looking at PE decisions, and why he felt prepared for a career with long hours.

Ward Bortz (‘06) grew up in a suburb of Milwaukee and played competitive tennis his whole life including his time at UofC where he was an All-American in 2005. After college Ward had various roles on Wall Street including a quantitative credit analyst, a high yield bond analyst, and a high yield bond trader. He went to business school at Columbia and afterwards moved to working in a quantitative type of asset management called factor investing and some of the world’s largest managers including Dimensional Fund Advisors and now BlackRock.


When did you start playing tennis? 

Deepak: When I was younger, I was always really into playing sports. I tried almost everything: soccer, basketball and baseball. However, I enjoyed the one-on-one aspect of tennis. I would always play against my dad. By the time I turned 8, I had already participated in my first tournament. From that age onwards, I would pretty much play in tournaments every weekend. At age 18, tennis had been a huge part of my life for so long, and I really wanted tennis to be a big part of my college experience.

Ward: I started playing tennis when I was five years old. My dad played, and he was interested in getting me to play as well. I remember my first grade teacher telling my class mates that I was a tennis player. My love for the sport and my competitive nature only grew with age.

What made you want to play tennis at the University of Chicago?

Deepak: Although I had always loved the individual aspect of tennis, I also wanted to feel like I was a part of a team in college. I had some experience being on a team in high school, but the main emphasis of schools recruiting you was on your individual performances and rankings from the weekend tournaments. I’m also from the Bay Area, and I wanted to come to Chicago to escape the Silicon Valley “bubble.” I wanted to move to a bigger city and become more independent; even though it was definitely uncomfortable at first. I really loved Chicago, and I’ve spent the six of the last eight years here.

Ward: When I was applying to colleges, I could not imagine my life without tennis. I had a successful career in high school and ended up winning two state championships. At the same time, I knew I was not going to become a professional tennis player. I decided on the University of Chicago because I enjoyed quantitative aspects of the college’s economics program.

Can you talk about what you studied at University of Chicago and how that helped you toward your first jobs?

Deepak: Coming out of high school, you never really know what you want to study or pursue career-wise. I ended up studying economics because business sounded both practical and interesting to me, and the UofC economics programs provided me with a rigorous problem-solving skill set. Also, the core program [a mandatory undergraduate program that includes classes in calculus, writing, language and science] allowed for a lot of variety in my schedule, which I felt helped round me out.

That being said, I learned more about business from internships. I never really use much from what I learned in my economics classes because there’s nothing quite like a real job experience. The summer after my third year, I had worked in investment banking. I did not fully grasp what investment banking entailed before I started, but the concept was intriguing. Investment banks act as intermediaries between investors (who have money to invest) and corporations (who require capital to grow and run their businesses). Investment banks also provide advisory services to corporations looking to engage in Mergers & Acquisitions activity. I saw it as a solid jumping-off point for other careers in business. I received a return offer to work at the same company after graduation in New York City. 

Ward: There was not a particular class that specifically peaked my interest, but the economics major classes provided me with a new way of thinking. Those classes taught me that understanding complex concepts was more about how hard you worked trying to solve them than how smart you are. Studying some of the complicated things we did at UofC gave me the confidence to not be intimidated by sophisticated concepts in my career.

The summer after my second year, I had an investment banking internship in Milwaukee. We helped school districts, cities and counties raise money via the bond market to build things like schools or fire houses. I did not know much about this sector at that point, but I liked the vibe. The internship taught me simple quantitative concepts like present value and I knew I wanted to continue down this path. The following summer, I worked in Credit Derivatives. I got to work with a PhDs and former professors modeling unique derivative trades. I enjoyed pushing myself intellectually.

Were you ready to leave tennis behind after graduation?

Deepak: My senior year we did really well as a team. It was, however, a really long season, and I was ready to take a break for a while. The fall after I graduated is when I first started to miss the sport. My teammates went back to train, and that’s when I became sad that tennis was no longer such a big part of my life anymore. The two years I lived in New York after graduation I did not really play at all. I was working long hours, and so it was really difficult to find people to play with in the limited time I had. There was a wall near my apartment, so sometimes I would go there to hit by myself. 

Ward: Although I loved tennis during college, I was not as nostalgic my last season. After my third summer working, I started to get an inkling as to what my future would look like and what career I would want to pursue. After the internship, I wanted to really enjoy my last year in college. During my last season, I was also very excited about my plans to move to New York City post-graduation.

Can you talk a little bit more about your transition and what that was like?

Deepak: When you’re a student-athlete, you naturally have to develop a disciplined routine. You create a schedule for yourself and manage your day-to-day tasks. When I started working full-time, I was pulling long hours, and it took me a while to develop a new routine. For example, I realized pretty early on that if I didn’t do the things I wanted to do early in the day, they likely wouldn’t happen, so I started doing things I wanted to do like reading and working out in the mornings. I think playing sports my whole life also gave me the discipline to take care of myself and my body. It really made me appreciate eating correctly and prioritizing getting enough sleep. 

Ward: When I entered the work force, I definitely felt that I was in over my head a little bit. I was working with PhD’s to decipher hard, complicated problems. What I learned from studying at the University of Chicago is that if you work hard enough, you will eventually figure a problem out. I used to spend six hours sometimes working out proofs in college. That attitude of pushing myself to learn paid off very quickly. As an athlete, I was already used to getting up early and developing a routine that was productive and efficient.

In terms of your transition, what was it like transitioning to finance?

Deepak: Athletes that have played sports in college are definitely ready for a career that requires long hours. We have always been used to juggling many aspects of our life and developing time management skills. Outside of the time management piece, you really benefit from the stamina developed from long days from an early age. Even though I never really used much from my economics degree, the University of Chicago econ major did teach me how to figure out how to do solve problems I had no idea what to do when I started. This was valuable in getting through investment banking as I generally knew very little about the tasks I had to do when I started in general.

Ward: Right now I am a strategist at BlackRock in Factor Investing. This means I explain this type of investing to clients and help them integrate it into their portfolios. A big part of what I do is try to explain hard, complicated ideas in simple ways. I’m paraphrasing but Richard Feynman once said something like “If you cannot explain the concept to a five-year-old, then you do not really understand it.” I like this sentiment.

Deepak, after two years, you moved back to Chicago to work in Private Equity. Can you talk about PE and what that change was like?

Deepak: In PE, the firm uses money from investors to buy, grow and eventually sell private companies. My company specializes in healthcare private equity, and a lot of my role now requires me to deconstruct all of the information about a company into extreme detail. We look to invest in smaller, private companies that have a solid business model and real potential for growth. I usually spend weeks analyzing the data generated and understanding the growth models. Knowing this information can help us decide how much we want to pay for the company or the company’s value. 

What is a project or company that you’ve worked on that you found particularly interesting?

Deepak: We were really interested in buying this Midwest company that specialized in improving the condition of kids with autism. We did three to four weeks of deep analysis on the company that would help us project how much we would bid for it. Right before the company was auctioned, we discovered a small detail that made us realize we were over-valuing the company. We lowered our bid and did not end up buying the company in the end, but it was cool to see our work translate directly to the decision-making process. When you’re analyzing the small details, it’s important to apply that to the big picture and not lose sight of the end-goal.

Ward, you decided to stay in NYC on the other hand. What drove that decision?

Ward: What I love about New York City is that it is where the majority of financial firms are located. If you are an expert in your field of finance, odds are you be in one of the buildings near Grand Central that I am looking out at now. I also love New York because it is an active city, and I had a lot of fun enjoying the city in my post-college years. I would definitely encourage college graduates to live here after school.

What goals do you have for your future?

Deepak: In the fall, I will be going to business school and am excited for the variety of people I’ll meet and the different perspectives I’ll develop. I definitely enjoy what I do now, but I also want to see what else is out there and develop the optionality to do different things in my career. Overall, I’m excited and imagine the variety of experiences I’ll have will be similar to my time at UChicago. 

What advice do you have for current student-athletes?

Deepak: You’re only in college with your teammates and friends for four years. It’s hard to replicate the feeling of playing sports at such a competitive level with some of your best friends. Although I play in tennis leagues still, it’s definitely not the same atmosphere. Playing sports in college also gives you an advantage career wise. The athletic network is a wide net comprised of many schools: I recently spoke with a Carnegie Mellon graduate who played tennis and tried to help connect him with employers. Recruiters really respect someone who went through four years of a sport while maintaining a decent GPA.

Ward: I remember hearing about a professor at Princeton who published his failure resume. If you read his traditional CV, it is as if he had never had a setback in his life. It was filled with fancy colleges, jobs and grants. But his failure resume was quite long! For each school he attended there were 5 rejections from equally prestigious intuitions.  I like the message he was trying to convey. I find some athletes who have been successful take “No” as “I am not fit for this job”. If you are rejected at first for a job, it doesn’t mean you are not cut out for that position. It takes a lot of rejection before you succeed.