Jessie Ai W'14

Email: Please contact Eunice Chong at chonge@wharton.upenn.edu for Jessie’s e-mail if you are interested in contacting her. 

What did you study at Penn and when did you graduate?  

I graduated from Wharton in 2014 with a concentration in Finance.

What were your favorite experiences at Penn?

Senior capstone was by far my favorite experience at Penn. It requires that you come back to campus from winter break early, but you essentially get to simulate building a business with a team through a video game developed by Wharton’s own game master. A lot of students gloss over the opportunity because it does require you to cut your holiday break short, but I highly recommend it. I also loved my WIP trip to South Africa during my spring break senior year. Wharton was able to pair outstanding cultural experiences (safaris, tribal experiences, museum visits) with meetings with notable Penn alumni. The trip was executed beyond what I would have expected or could have planned for myself.

What did you do after graduation? 

After graduation, I went to work for Jefferies in their Healthcare Investment Banking group for two years as an analyst and one year as an associate. Afterwards, I moved back to Philly to work for the Hamlin Family Office, the family office of a Penn alum, for three years. Then, I moved on to the Forman Family Office, where I currently serve as the Head of Investments.

What is your biggest accomplishment?

My biggest accomplishment is the people I surround myself with. I have been fortunate enough to stumble across amazing mentors in every stage of my career. It is critical to find mentors early on and to challenge yourself to be authentic and vulnerable with them. 

How has being a woman in business affected you and your career?

While it is rewarding in many ways, being a woman in a male-dominated industry comes with its challenges. You are often excluded from networking and bonding experiences, such as golf outings or happy hours, that are awarded to male peers. It has also been difficult finding senior level female mentors. Knowing my experience, I try to help other women early in their career so they can learn from my mistakes. Additionally, it is often hard to find your voice when you are a “token” or “double token” (being Asian and a woman) in a room. It took me well into my late twenties to truly find my voice.

What is the worst advice you have ever received?

“Just do it for the money.” If you find something you truly love to do, wealth will come. 

How do you balance your personal life, hobbies, and work?

I’ve found that if you do what you love, you don’t have to carefully delineate across the three categories. My career now gives me the flexibility and platform to invest in industries that are interesting to me and participate in efforts that are meaningful to me. When I was at Penn, my largest involvement was with the Cohort System. I was Shekel’s cohort director, VP, and then President. I also belonged to various business groups such as PEVC Club, WCBS, and WUGS and was a sister in Sigma Kappa. Now, I spend a lot of my time spearheading collaboration in my peer group across the city and participating in female empowerment initiatives through Women’s Way and the Forum of Executive Women. I also find time to pursue my interest in art by sitting on the Young Professionals Leadership Board at the Barnes Foundation.

What advice would you give to a current undergraduate?

I would tell an undergraduate to think outside the box. It is really easy to get into the herd mentality and feel pressured to go into finance or consulting. It is super important to acknowledge passions early on. I have found that many of my classmates who took unconventional paths that followed their own interest areas ended up happier. Unfortunately, that’s not a piece of advice that I took to heart, but I eventually left investment banking to prioritize my mental health and happiness. 

How would you recommend that a student doesn’t “follow the herd?”

First, I would recommend that you reflect internally. It’s important to recognize that you are living your life and need to answer for yourself first and foremost. Is the additional hour per month of bragging about working for McKinsey or Goldman Sachs a sufficient trade off for being unhappy on a daily basis? Second, try new things. I am a big believer in trying everything once before forming an opinion. Third, be open-minded. Be generous with your time and don’t write anybody off until you get to know them.