So, you want to work on Wall Street?

Black Enterprise, Oct, 1996

DEAN: And they still do. That is why the industry is losing people to consultancy. The first choice [for people aspiring to a career in finance] is private equity. They can make more money while working less.

SHEPHERD: I think that individuals are attracted to Wall Street for its environment. It's about the desire to win. There's a subtle litmus test when we interview somebody: Does this person really want to be here? Do they know all of the characteristics that you need to survive here? And when people are comparing all of those other job options, I think there's a clear subset of those who are going to say no to Wall Street.

DEAN: But the question was, What advice would you give that kid?

THOMAS: I can answer this one. Every morning you wake up and get out of bed and you've got to either want to go to work, or not. I tell you, the majority of times, I really want to.

DEAN: But our competing industries are going to say the exact same thing.

THOMAS: I hear you but let me tell you: What drives me is that in the morning, I walk in and I'm competing at the highest level in a very dynamic environment. I'm playing a new team. I'm playing against x company, z company, y company, all competing for the same thing. Constantly changing markets make it a new day every day. You can be entrepreneurial, and that's important. Second, you have the opportunity to be on the winning team. You can be the person who, at the buzzer, takes the last shot and becomes a superstar. And sometimes, you're going to be the person who, in the last three seconds of the game, passes the ball to the person who makes that shot, so you have a support role and--boom--your firm won. That to me is great.

SHEPHERD: Yeah, but you have to want the ball.

IVY: Absolutely. And if you're not that type of person, this is not for you. If you're the type of person who would go out and start your own company with your own money, you would probably be more disposed to this industry versus some other.

BE: When will you know it's time to retire?

DEAN: This is not an industry where you see a lot of 55-year-olds. You see almost no 60-year-olds. Most senior management, at almost every firm, will be in their 40s. It's a young business, and that's because people work very, very hard for 20 or 25 years and then burn out. More importantly, you can't ignore the fact that if you stay in the industry that long, you'll have enough financial security to say, Let's go do some other things.

SHEPHERD: When you get to our level, you should have made enough money so that you can walk away saying, I had a good run on Wall Street. You spoke about waking up every morning and being inspired to face all of the pressures that one has to deal with on the Street. To me, that has always been the big barometer. I like what I do. I get up every morning and I want to go to work. I like the competition, working on the hard deal to beat the competitive firms, and I get joy when we do that. When I don't do it--because you don't win all the time--I want to get back into the batter's box to do it again. So to me, the whole thing has been, Do you still like it? But you have to be able to deal with the lack of job security on the Street. Every year it's a new deal, and you got to be ready to deal with that. If you can't, then you need to get out--and they'll put you out real quick if they notice that that fire isn't there.