meet carolyn: trailblazer in chicago’s financial industry

“Some of the guys thought that because I’m blonde, I was dumb. So they would talk about their trading strategy in front of me. And I would just listen and absorb everything they were saying.”

Carolyn Leonard, DyMynd, People with Panache

Carolyn’s philosophy on investing: “Diversity does go to the bottom line: all diversity – racial, gender, sexuality. If you’re looking to invest in companies that will outperform their peers, look for diversity and depth of experience in the C-suite and the board of directors.”

Way to turn lemons into lemonade and jerks into teachers, Carolyn!

In some ways, Carolyn Leonard’s story isn’t uncommon. She entered a “man’s world” and was treated brazenly unequally—but that’s where any notion of Carolyn being average ends.

Carolyn, 73-year-old entrepreneur and founder of DyMynd, says in America there are 9.2 million women-led companies with an economic impact of $3 trillion. While discrimination like she experienced keeps lingering longer than seems acceptable or necessary, we women can change it—together. And we are.

As one of the oldest entrepreneurs in the country, Carolyn is a real-life testament to facing your fears, taking risks on yourself, and never giving up. From being one of the first women to trade on the Chicago Board of Options Exchange to starting her own business four years ago at age 69, Carolyn’s story tells itself.

Carolyn Leonard: Like most women of my generation, I got married shortly after college at 22 years old. I was considered an old maid at that time. I had several girlfriends who got married after high school and already had children. I also knew from a young age that I had to go to college because my mother got her master’s degree in 1936. My grandmother also had a college education.

My mother used to say: I own you until you graduate from college. She had my ass on lockdown. At that time, when women applied for a job, they could be asked, “Are you on birth control? Are you going to get married?” An employer could ask about your religion or how many years you saw yourself working because they didn’t want to spend a lot of money training you.

I got my bachelor’s in business, went to graduate school for education, taught for a very short period of time, got married, and had two kids. Fast forward to 1976, and my marriage is falling apart. I’m married to an extremely successful trial lawyer—a senior partner with one of the largest law firms in the city. He’s somebody that nobody can win against. I knew that I had two children, a fabulous lifestyle, and if I wanted to continue that lifestyle, I would have to do it myself. So I looked around at the people who lived in my neighborhood to think of careers where I could potentially make a living using skills I already had. There were these new guys called traders. What were they trading? Soybeans. I had no idea what soybeans were, but I just knew if you traded soybeans, you made a lot of money.

So I decided I was going to become a trader. But I didn’t want to trade soybeans or any other commodity because I didn’t understand them. I understood stocks, and we had the Chicago Board of Options Exchange. I was going to be an options trader. That was it.

I went downtown to the CBOE, met a friend on the trading floor who signed me in, and proudly announced this is where I was going to make my living. I knew nothing about what an option was, but I knew this was a place of opportunity, and if I could do this, I could stay in my house and my kids’ lives would not be disrupted. My first question on the trading floor to my friend was: Who’s the smartest person down here? Everybody agreed on the Ph.D. who taught math at the University of Chicago. He had come down on the floor three years earlier and made an obscene amount of money. He gave up his teaching career, but he still knew how to teach. I asked to be introduced to this gentleman, and I told him I was getting divorced, I had two kids, I had to make my career work, and I was going to be an options trader, but I didn’t know anything about it. He said he occasionally takes on and mentors a clerk if I could be there at 6am and leave at 6:30 at night. I ran to a phone to call my mom to move in because I had the children. And I was tutored by him for 2½ months.

During this period of time I took the SEC exam to become licensed. I got a broker dealer, and I bought a seat. I had a real problem because I never had credit in my own name as most women didn’t at that time—all the credit was in a man’s name. I had a mother fortunately who had credit in her name because she owned real estate, and she cosigned a note for me to buy my seat and put money in my trading account. I owed my ex-husband for his half of the house, and I had a mortgage. I was a quarter of a million dollars in debt and had never made a trade. I didn’t think I had a problem.

Carolyn, PWP

How did you get through it? “I was very focused on the fact that I had to make a living. I wasn’t thinking directly about the fact that these people really don’t like me. I wasn’t going to let them get to me, that there was nothing they could say or do that was going to shake me.”

Ignorance is bliss. I was totally blind to the fact that the failure rate was in the upper 90th percentile. In the face of needing to make money and needing to make it quickly, I embarked on my trading career. Everybody was very nice to me as long as I was a clerk. The minute I was going to trade with them, it was like the door slammed on me, and men told me point blank they’d never traded with a woman—don’t take it personally, but I’m not going to trade with you. How would I get people who don’t want to work with me to work with me? Most of the men didn’t work for companies where you could talk to somebody and say, “This is discrimination.” They worked for themselves in an environment that was open outcry, which meant because everybody yelled their bid or offer, they could always say, “I didn’t hear you.”

I decided to use the one thing I had as a woman: I wore clothes very, very well, and I already owned the clothes! So I started dressing beautifully for work. And in doing that, I was able to attract business not from the men in my pit, but from the people that came in from Merrill Lynch or Goldman Sachs or Neiman Brothers around the floor. They didn’t know that they weren’t “supposed” to trade with me. They would make the mistake of talking to me because I had something nice on or something they thought was pretty. Because they were talking to me, they would do business with me and that was enough to sustain me for six months. Although I wasn’t making a lot of money, I wasn’t losing money, and I was learning and getting much better at my job.

Then, one morning in April, I arrived on the floor, and there was a lot of to-do in the 3M pit that I traded in. There were hundreds of people gathering around the pit, and I was informed that 3M, which had closed at $44 on Friday, was opening on Monday morning at $52. All the orders in the pit were buy orders, and there were only two other people who traded 3M besides me. These two other men had invited me in to divide the risk when I first started trading. They didn’t want to assume all the risk themselves. So when the imbalance of orders happened, one of the men told everyone: It’s over. Either you’re going to trade with the fucking broad or we’re not trading with you.

That’s a direct quote. From that moment on, everybody traded with me. And the embargo against me was broken. That day was my most successful trading day. At the end of that week, I had six figures in my trading account, and I never looked back. I traded for 21 years. I moved into much larger, more competitive pit environments where the competition was fierce. Nobody ever said they didn’t hear me. In fact, guys eating in the cafeteria on the floor above would complain they could hear me upstairs. But a girl’s gotta do what a girl’s gotta do!

After the first year of trading, I out-earned my ex-husband. That felt fabulous. I consistently out-earned him and most of the men I traded with. It afforded me a lifestyle and an opportunity that no other career could have at that time.

Now, because I was a woman and dressing very fabulously, of course I had three-to-four-inch high heels on, which were dual purpose: One gentleman elbowed me so hard, he got my spiked heel on his instep. It was such a terrible accident, I feel terrible to this day—but nobody ever poked me again.

The other advantage of being a woman in a man’s world: Because I wasn’t allowed into the middle of the pit, I had to stand on the fringes. There, I was closest to all the traffic coming out of the trading booths that circled the floor. On busy days, I started to feel this odd sensation going up the back of my legs—like a vibration. The first few times it happened, I really wasn’t aware of it because I would get incredibly busy and start to trade. By the third time it happened, I thought: Vibration up the leg, very busy trading—we now have a correlation. So I began to listen, and I would either buy or sell depending on what I heard. I would be ready when that market exploded, and it gave me about a three- to four-minute advantage. And I capitalized on it.

People with Panache: Your story is unlike any of my generation. You were pioneering the way for women traders! And I love that you never forgot who you are—never lost your identity. You didn’t try to act like the men or be someone you weren’t. I think women often make the mistake of trying to fit in or be heard by not being themselves. So after being a successful options trader for 21 years, what did you do next?

CL: I looked around the floor and saw that I was twice as old as anybody down there—the average age of a trader is 27—and I decided that it was time to hang up my pink trading jacket. I started working in my husband’s office in commercial real estate, but I always missed the financial services industry and the investment industry.

Carolyn Leonard, DyMynd, peoplewithpanache.com

I asked her what it felt like to be the only woman on the trading floor: “It was very lonely. When I started trading, there was nobody to talk to really if I had a problem without sounding like I was whining. It was really the first time in my life I totally understood what being an outsider was. I understood that I wasn’t wanted, that they were angry I was there.”

Always putting myself in business and working for myself, I knew I wasn’t going to go work for somebody else. In 2008, the light bulb went off for what I wanted to do next. When the market crashed, I began to get calls from my girlfriends asking me what they should be doing because their portfolios were now falling apart. They had half the money they had a year ago, and they were scared. Everyone was scared. I was scared. I know from trading and from life experiences that when it comes to money, it isn’t rational—money is very emotional, and because it’s emotional, it plays on our fears.

I knew there was an opportunity for me if I could better understand behavioral economics and the psychology of stock markets. When I started learning more about the industry to see what types of products were offered for people from the behavioral economics point of view, I discovered that by and large the industry had the old model: Markets are rational and market participants are rational. I knew that wasn’t true, so I decided I was going to create a company that would look at how people feel about money and create an assessment to help people better understand who they are around money—to create the total picture of the psychological makeup of an investor. Then I could educate advisors as to how to talk to people about their money from the emotional point of view as opposed to the risk profile.

I started DyMynd in 2011. I was 69 years old, and I’m 73 today. You’re never too old for a good idea or to become an entrepreneur.

We geared it toward women because the growing wealth of women is astounding. By 2020, women will control $22 trillion of assets in the US. By 2030, they will control 2/3 of all the assets in the world. So I knew that we were going to focus on women. That’s the underserved market, and it’s the growing market.

PWP: What do you think got you to where you are today?

CL: One of the reasons I was good at my job is the fact that when I was young, I had ADD. When I came on the trading floor, I didn’t realize that successful people down there were my people. They had ADD. ADD doesn’t go to intellect in brains, it goes to brain wiring, and people with ADD can keep track of a lot of balls in the air or a lot of information at once. They’re able to understand where everything is and can retrieve that information when they need to in order to act and make a trade. Whereas in school, being ADD was a disadvantage, in my work environment, it was an extreme advantage.

PWP: What advice do you have for other people who want to be pioneers in their field?

CL: Don’t be afraid to take risks on yourself. The best investments I ever made were in me. Whether it’s education or other things, take a chance on yourself. Don’t let somebody tell you no. You can do a lot more than maybe you think you can, and if you don’t try you’ll never know. I was never afraid to fail. Failure is part of the process. I didn’t know that I would be successful—I just assumed I would be. And I did it.

You always have to step out of where you’re most comfortable. So what if they don’t like you. Who cares. I like me.

[Photos provided by Carolyn.]

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