From Private Equity to Business School and Back Again.

Tales and advice from a recent Booth alum who’s been through it.

For anyone who has ever considered a career in private equity, wondered whether business school was the right (or only) way to get you there, or thought it was a necessary next step in your career… keep reading.

The Polsky Center recently turned to Booth alum, Donnacha O’Sullivan, MBA ’17, to get all of these questions answered and more. As someone who has been down the PE to MBA path and back again, he speaks openly and candidly about the most commonly-asked questions current and potential MBA candidates ask regarding access to the PE industry — both as industry incumbents and as hopeful career-switchers.

Polsky: What made you decide to pursue your MBA?

O’Sullivan: My job before school (PE associate) was a 2–3 year program that traditionally culminated in business school. Most of my bosses and mentors attended business school (several attended Chicago Booth), and each conveyed how transformative the MBA was in their life and career. After working in investment banking and PE for six years, I believed that the MBA would provide access to a broader community outside of financial services. I also felt an MBA would allow me to learn more about non-finance roles (e.g., entrepreneurship, sales, health care). Lastly, I was hoping to gain private equity investing best practices through my classmates and internships.

Coming back to the PE industry, what’s been the biggest advantage that your MBA has provided you?

Confidence. Before school, I was fortunate to have the opportunity to be a fly on the wall with Fortune 500 directors and executives. At the time, I would have been the youngest person in the room by 20–25 years. It is easy to feel like you don’t belong in those meetings and be shy. You can learn a lot at that age by listening vs. talking. However, after graduation I now have the confidence to speak up and I feel comfortable that my contributions in those meetings are valuable to the organization.

What’s been the biggest takeaway or learning that you’ve brought back to your career?

Evaluating and advising businesses is much easier than building a business and going out selling that solution. I am not certain what my peers in investment banking, consulting, academia, and investing will think about this, but I have quickly appreciated the significant battles my friends have encountered as they pursue careers in operations and entrepreneurship.

If you could do one thing differently during business school, what would it be?

I would have been more thoughtful and deliberate with how I allocated my time. I would have invested more time building something. I would have loved to go through the NVC (New Venture Challenge) or do a search fund during my two years. It is easy to spend time doing something you are good at. And, if you are at Booth, you are probably already good in the classroom. I personally feel like I have learned more from my real-world experiences than from books or classes.

Also, the time goes by fast. Try to figure out something you are personally passionate about. Once you find it, stop overthinking it and just start doing it. I really wanted to co-write a play with my brother, who is an actor. I thought about writing a lot, but I think I got all of two pages done in two years. On the other hand, I made some personal sacrifices working in finance for six years and I was very glad to spend a lot more time with my family during business school.

What is the biggest piece of advice you have for anyone considering business school as a way to access a career in private equity?

Save money and get a 3–6 month private equity internship before school starts. If it is possible, I would advocate delaying business school and taking a pay cut to work in private equity as an analyst or associate for two years. I think too many students think business school has a job board that connects you with private equity employers.

First, that job board is ultra-competitive. The entrepreneurial students who hustle (i.e., don’t rely solely on the job board) and have a bit of good luck are the ones who end up with private equity internships. That is the same skillset you’ll need to get a pre-MBA private equity job or internship. Also, the job board doesn’t really kick in until your second or third quarter. At that point, you have likely made a big bet on doing private equity for the summer. For example for Booth students, what happens if you are fortunate enough to get into Booth’s Private Equity and Venture Capital Lab in the Spring quarter and you realize that private equity isn’t for you? You’ve missed the boat on a lot of the traditional recruiting opportunities. On the other hand, you are left scrambling for a summer internship in the final few weeks if you realize you do enjoy private equity. If you can gain some private equity experience before school starts, it will ensure that you’re pursuing a career that you want and leave you better off for recruiting.

If it is not possible to attain a private equity internship or job before school, I would encourage you to spend a lot of time talking to people who accessed a career in private equity through business school. Don’t be hesitant to ask the challenging question, “What is the likelihood of me getting to the other side?” Make sure you are comfortable with the low odds (<10%) or appreciate what levers (e.g., pay cut relative to your classmates, geography, etc.) you are comfortable sacrificing.

What is the biggest piece of advice you have for someone already in PE, considering business school like you did?

Don’t follow the track just because everyone else is doing it. I would urge you to invest time and ensure you want to stay in private equity for the right reasons. Also, evaluate why business school is the right choice for you. If you aren’t certain private equity is right for you, you might look at business school as a safe place to explore other career opportunities. Lastly, develop a view for your personal investment philosophy and go find a firm that aligns with your belief system.

What was the most valuable experience or program you participated in at Booth?

All of the experiential learning opportunities and internships. Entrepreneurial Selling required our team to develop a sales strategy for the NVC alum company, ExplORer Surgical. We subsequently cold-called potential customers on their behalf. It provided a much better appreciation for the difficulty of sales roles. The Oxford Chicago Global Private Equity Challenge case competition required our team to present to an investment committee comprised of distinguished private equity investors. I also did the Sterling Partners Investment Thesis Challenge and the Private Equity and Venture Capital Lab with Flexpoint Ford and Tyree D’Angelo Partners, respectively. I had a chance to spend my summer with Sterling Partners and one of their portfolio companies. The investment professionals and executives at each of these firms taught me so much. The lessons dispensed from Steve Kaplan, Chris McGowan, and their guest speakers rounded out my investing toolkit. Lastly, I did the Management Lab with a group of students (MBAs, medical students, and PhDs), where our team served as consultants to a biopharmaceutical company. This 10-week engagement required us to assess the attractiveness of potential new drug therapies and recommend an acquisition strategy. It is thrilling to know that all of the “homework” for these classes led to investors and executives pursuing plans for their businesses based on our work. In addition to the real-world education, each of these projects required presentations and further improved my public speaking confidence.

Donnacha O’Sullivan is a Vice President at TTCP. He is focused on investing in high-growth healthcare IT and service businesses. Donnacha has a broad experience developing and implementing strategic initiatives alongside management teams. Prior to joining TTCP in 2017, Donnacha spent three years at Baird Capital, where he invested in several healthcare IT and service businesses. Donnacha was previously a healthcare investment banker at Piper Jaffray.

Donnacha earned degrees with High Honors from both the University of Illinois (BS) and the University of Chicago Booth School of Business (MBA).