In our series “Jump-start Your Job Search,” Bostonia brings you short interviews with BU alums who are leaders in their field, such as banking, advertising, tech start-ups, journalism, or nonprofit organizations.

They talk about how they got to be where they are, mistakes they’ve made, and what they’ve taken away from those mistakes. They tell us what they look for when hiring and offer advice for those just embarking on a career.

This week, our featured alum is David Buttolph (CGS’77, CAS’79), founder, managing partner, and comanager of Brookside Mezzanine Partners, a private investment firm that manages more than $500 million across three funds. The firm makes debt and equity investments in small and midsize companies to support buyouts, acquisitions, and growth. Prior to founding Brookside in 2001, Buttolph was a partner at Canterbury Capital Partners, a middle market mezzanine investment firm. Before that, he was a senior vice president at LaSalle Business Credit, Inc., and a district manager/vice president of Barclays Business Credit, Inc. He began his banking career at Bank Boston.

Buttolph graduated from BU with a degree in psychology and earned an MBA from Suffolk University in 1980. His two daughters, Kristen Buttolph (CGS’10, COM’12) and Amanda Buttolph (SED’11), are also BU alums.

Bostonia: What are the qualities you look for in people you hire? What are the deal breakers?

Buttolph: Has the candidate had meaningful internships in college? Have they prepared questions for me and my team? Have they shown up with extra résumés and a pad of paper? You cannot believe how many candidates show up empty-handed. Have they researched what mezzanine debt is? Do they have a passion for investing and learning? Can they articulate why they want to join us?

What kinds of questions do you ask during an interview?

I start with: “You have three minutes to tell me about yourself and how you ended up in my office.” I then ask what they know about our firm: “Can you tell me about some of our investments?” If they cannot speak to any portfolio company, I ask where I (or the team member interviewing them) went to college. It may sound harsh, but if you are applying to be an analyst at Brookside, you should have analyzed BMP and our team in depth, or it is a very short interview. I also like to know about what they have done summers, including in high school. I like to see that they had high school summer jobs and worked hard. I washed buses, cut lawns, and painted houses.

When you were in college, did you have an idea what you wanted to do for a career?

Nope, I thought I wanted to be a doctor or a marine biologist.

How did you come to work in this field, and why?

After getting my degree in psychology, I decided I really wanted to work in the financial field, so I went to Suffolk University at night. I got my MBA in finance while I sold computer accessories during the day. I then applied to the three big banks in Boston, and I landed an entry position at Bank of Boston. Over the years I worked my way up at a couple of different banks and then made the switch to mezzanine financing. I wanted to start my own firm, and with backing from several wealthy families, I started BMP in June 2001. We now have 167 investors and over $500 million under management.

What advice would you give to someone interested in your industry?

Try to manage a portfolio or participate in an investment club so you can start thinking about investing as a career. Whether you make or lose money is OK as long as you learn from the experience. Also, try to get internships in the financial field.

What expectations do you have for new employees?

High. We are big believers in total immersion. You are immediately presented with new investment opportunities and are expected to present your thoughts and conclusions at our weekly Monday partners meeting.

What’s the competition like for new graduates in this field?

Fierce. Assuming you are invited back from the initial interview, you will be given an investment opportunity to study for a week and then you are invited in to present it to the entire team. If that goes well, we then give you an office to construct a financial model from scratch with a three-hour time limit.

What mistakes have you made during your career, and what lessons have you learned from them?

I stayed at a firm that had an unhealthy culture for several years too long. If you find yourself in that kind of situation, or you are not learning new things or enjoying your job, it is time to move on.

What advice would you give for the first six months on the job?

For the first six months? Don’t be shy about asking questions. You will be drinking from a fire hose and no one expects you to know everything. If you are not super-busy, ask for more work.

Who has had the greatest influence on your career, and why?

My dad, a classic entrepreneur who started several companies and was not afraid to fail.

Are you an alum who would like to be interviewed for Bostonia’s “Jump-start Your Job Search” series? Email John O’Rourke at orourkej@bu.edu.