Wall Street’s toughest octogenarian woman

February 4, 2013, 8:35 PM UTC
Muriel Siebert in 2011.

FORTUNE — Muriel “Mickie” Siebert has been known as the “First Lady of Wall Street” for almost two generations. She was the first woman to own a seat on the New York Stock Exchange, paying nearly half a million dollars in 1967 for the privilege. (She says she borrowed the majority of it, from Chase Manhattan, after David Rockefeller personally approved the loan.)

At the time, there were 1,365 other members, all men. SKIRT INVADES EXCHANGE, proclaimed a headline in a Montana newspaper. One male securities analyst explained to a Baltimore journalist that “women spend an awful lot of time trying to manage their husbands, so they have a natural advantage” in “picking good investments.” On its front page, the New York Times, quoting unnamed friends of hers, described Siebert as “bubbly and ebullient and fortyish.”

Despite such inane commentary in the press, she thrived, both in terms of professional reputation and financial success. Ever since — through business peaks and valleys, entrepreneurial adventures and philanthropic efforts, public service and personal challenges — Siebert has been seen as a crusader. Some women have considered her a role model; others, irrespective of gender, have simply viewed her a prescient and colorful character of the financial world. She knows her stocks and she knows how to read a financial statement, but she especially likes to boast that she learned to use four-letter words when dealing with traders — and has never lost the knack.

Born and raised in Cleveland, the 23-year-old Siebert came East in 1954 in her old Studebaker, with no college degree, $500 in her pocket, and only the dream of a life on the Street. As a teenager, she had visited the NYSE (NYX) with her family and, looking down from the balcony from the Exchange, she was instantly taken—perhaps not unlike a boy of the time who first cast eyes down upon Yankee Stadium from the bleachers. After being turned down by Merrill Lynch because she hadn’t graduated from college, she fibbed that she had a degree. Thus she was able to launch her career as a $65-a-week trainee in the research department at the brokerage firm Bache & Co., eventually specializing in the airlines and aerospace industries. Later on, she became a partner two other securities firms, Finkle & Co. and Brimberg & Co. For five years, beginning in 1977, she served as superintendent of banking for New York State — the first woman to hold the job, which she calls “S.O.B.”; a lifelong self-described bleeding-heart Republican,” she was appointed by a Democrat, then Gov. Hugh Carey. She also had a failed run in a G.O.P. primary in New York State for the U.S. Senate in 1982.

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Now 80, she still runs Muriel Siebert & Co., the seven-branch brokerage house she founded when she bought her NYSE seat. The firm was a pioneer in discount brokerage, in time going public (SIEB, for the Siebert Financial Corp., on the Nasdaq). The firm isn’t what it used to be and its stock rarely trades, but Siebert still is at work most days, with the cable financial shows always on in the background. In her 17th-floor office in the Lipstick Building in midtown Manhattan, Siebert recently sat down with Fortune to look back on her storied career. With her beloved Chihuahua, “Monster Girl,” in her lap, and surrounded by framed magazine stories (including in Fortune) and photos of herself with American presidents, Siebert talked recently talked with about risk-taking, feminism, ethics and her nonprofit financial-literacy program that today is part of the economics curriculum at many New York City public high schools. Edited excerpts:

What do you know now that you didn’t know 50 years ago when you drove your Studebaker here?
I think I’ve been exposed to a wide variety of people and learned a lot about people that I wouldn’t have learned in Cleveland Heights.

Good things or bad things?
Well, there are good things in people and there are some negative things in people.

Are we talking about Madoff or Enron or the financial meltdown in 2008, or all of it?
For the amount of business that’s done, there are relatively few problems. But the public doesn’t have the same information it is entitled to. The volume of trades goes up and up, but there is less and less transparency. Transparency is what always set our markets apart. I don’t see the same ethics on the Street as when I came in. They trade offshore, they trade in “dark pools” off of public exchanges. It’s unfair.

When do you mark the beginning of the change?
I was complaining about financial things that I couldn’t understand in our industry 15 years ago. Like derivatives. There are a lot of people that have made a lot of money — and they aren’t geniuses. And yet some of them just look at themselves and say, “I am the great I am!”

If you were young again, would you still come to Wall Street to find your way? Or might you drive to somewhere else, like Silicon Valley?
Maybe if I had the talent I’d go out there. I mean, Wall Street doesn’t have the same opportunity. There’s no floor anymore.

Apart from the one visit to the New York Stock Exchange, what else brought you to Manhattan?
I was always good at math. I happen to have a mind where I can look at a page of numbers and they tell me a story. I understood financial statements from Day 1. My older sister Elaine also was here.

On Wall Street?
She moved to New York after a divorce. She became a vice president of an advertising agency. So I had a place to sleep: her couch, in a two-room apartment in Tudor City.

When you arrived, Wall Street was not particularly open to women.
No, it wasn’t. And there was anti-Semitism as well.

There were firms that I would not even apply to for a job.

I’m a Jewish woman. I mean, forget it.

How could they know for sure if you were Jewish?
In those days you were always asked what your religion was when you applied for a job.

Could one fib about that?
I couldn’t.

What was it like coming to New York back then?
There were many women who would stay for six months or a year, and then go back to where they came from. But I found New York was a toy. I was close to my sister. And I got a job at which I had a talent for.

You didn’t have the job when you first started.
It took only a couple of weeks. Firms were looking. When the economy is good, Wall Street expands. And research is the first place where they used to expand.

And the college-degree thing?
I had applied to Merrill Lynch. They asked me, “College degree?” I said, “No.” They said, “No degree, no job.” So the next day, at Bache, they asked, “College degree?” And so I said, “Yes.”

You didn’t own up to your lack of a college degree for years — until you sought your seat on the Exchange. Why?
I had to do that to get a job. I was dependent on it.

Wouldn’t you fire an employee who lied to you?
It would depend on what they lied on. If they had a violation of ethics and didn’t admit it, then I would fire them because I’d say they’ll do it again.

You developed formidable expertise as an analyst, didn’t you?
I was at Finkle & Co. I heard from Davey [Finkle] that “Mr. Johnson” [Edward C. Johnson II, the founder of Fidelity Investments] was fuming because none of the funds would listen to the boss to buy a stock that he thought was cheap. So, Davey said to Mr. Johnson, “I’ll have Mickie check it out for you.” Davey called me and I went to Detroit to see some company that was making milk-vending cartons. I called Mr. Johnson from the airport, who then had me on the phone for two hours. I was furious! I missed three planes coming back. People realized that I studied and knew the companies, and I did more and more business.

You worked with many of the old characters of Wall Street?
I was at Brimberg & Co. for three years with the late Bob Brimberg. He was an embarrassment. I mean, he used to tell dirty stories all the time. And he had a father who used to sit with a bottle of scotch on his desk — he had permission from the New York Stock Exchange to keep it because he had a heart condition. But Bob had an institutional business, and I got to know a lot of the institutions while I was there. He used to be called “Scarsdale Fats” [and was identified as such in Adam Smith’s 1967 bestseller “The Money Game”].

Why was he “Scarsdale Fats”?
Because was fat and he ate like a horse. And he lived in Scarsdale.

What did you learn from Brimberg?
Bob was very creative. He used to have these luncheons for representatives of big investment institutions. He’d say to people like me, “Mickie, tell them about XYZ Company that you just saw.” Bob even offered me my name in his firm if I would stay. But I wanted my own seat on the Exchange.

Do you have a sense of when you first began seeing yourself as a trailblazer?
It’s not like I was thinking early on, “I’m going to join the Exchange.”

Where did that idea come from?
I went from being a research analyst to placing orders for clients. But I wasn’t getting paid the commissions men were. I was getting half of what they got for the exact same orders. So I asked a client, “Gerry (Tsai, of Fidelity Investments], where can I go that will pay me equally?”

And what did he advise?
He said, “Don’t be ridiculous! Buy a seat and work for yourself.” And I answered right back, “Don’t you be ridiculous!”

It was such an outlandish idea?

How much were you making at the time?
Maybe $400,000 to $500,000.

You had to borrow a big chunk to buy the NYSE seat.
Sure I did. Back then, $445,000 was a lot of money…Do you see this Mexican gold piece I’m wearing around my neck? I was having lunch with someone at Chase Manhattan on the day that I put my bid card in for the Exchange. He said, “Carry this for luck.” And I’ve had it ever since.

Did you wind up getting paid more by working for yourself?
More important than that, I had control over whom I did business with.

For the retail part of your business, did customers come simply because of the low commissions?
The rates, and the fact that you don’t need a computer to work with us. We have live brokers — they’re registered reps.

So it’s convenience more than supposed expertise in Apple versus Intel?
And we do have a pretty good ability, because I did a lot of institutional business, of executing orders.

You eventually decided to take your brokerage and underwriting firm public in 1997. Why?
Yes, as a way to expand. It wasn’t about the money.

As newspapers pointed out, you were once a paper billionaire — in 1999, during the bubble, when the stock prices of online brokers were surging.
Let’s forget that. That was so long ago. [The stock peaked at $52 in April 1999; throughout 2012, it was under $2.]

Why did you go public in such an unconventional way — through the back door, by merging with an already-listed company that was going out of business, rather than by raising money from the public? You were criticized for it.
It was fast. I didn’t have to have a minimum size; f you go public, you need to raise X dollars. And this way I didn’t have to sell anyone anything. My accountant happened to also be the accountant for the furniture store in Brooklyn [J. Michaels] that we merged with. “It’s a clean shell,” he told me.

How much of the company do you still own now?
I own 90%. The stock trades occasionally, but the business has changed. Had I known, I probably never would have gone public.

How has the business changed?
I had thought having a public company would be great because I’ll be able to buy other things, grow my firm. But you couldn’t do that when the commissions became really discounted — a penny-a-share. Profitability ran out the door.

Are you profitable now?
We’re not. I’ve had an arbitration going on for six years. I’ve already paid $15 million in legal [and other] costs. An executive that was very important to this company at one time, [COO] Nick Dermigny, basically wants an amount equal to the value of the whole firm. [When contacted, Dermigny’s lawyer denied that his client was seeking that amount.]

A total of $15 million sure sounds like hefty fees for an arbitration.
You’re telling me — it’s half of my f—ing capital in the company! It’s also forced the firm to go into the red at times. It’s a horror show.

I assume the arbitration means you have less money, as well as time, to put into your philanthropic efforts?
Right, it’s money going down the drain. And it’s energy that has forced me not to do other things, like my small foundation, which has about 14 million bucks in it.

What got you interested in advocating for financial literacy for teenagers?
Yes, that’s the thing I’m most passionate about now. I started the Personal Finance Program when I was superintendent of banks, I would meet these 17-year-olds who were ready to go bankrupt because they were maxed out on credit cards. The program is taught in 100 schools in New York City. We’re in Florida, too. My goal is to make it national. I go to the schools and speak. It changes kids’ lives. You can’t understand it until you see it yourself.

Do women still come to you seeking advice and a mentor?
They would if I opened the door a little bit. But where would I get the time? I’m putting all my energy into the financial-literacy program.

Does your sister still live in New York?
She is, but she’s in an institution. She can hardly talk now. She had a hysterectomy decades ago and she went bad mentally. I’ve supported her.

You took care of your mother as well, right?
Yes, she moved to New York. I supported her, too. She lived with me for a while, and then I had her in her own apartment when I could afford it. Those were tough years. You step up to the plate. I couldn’t run. [Siebert’s mother died in 1976.]

You’ve spoken about the difficulty of managing it all.
I was running a business when much of this was happening. It was all-consuming.

You’ve also mentioned that drinking too much didn’t help.
I knew I was drinking more, but I had so many pressures.

Did alcohol interfere with work?

How did you solve the issue?
I stopped on my own. I just decided that I had to cut it back. I mean, I still have a drink, but it’s not an issue.

Do you think that family issues were a reason you never married or had children?
I almost married one guy back home. I went with him for three years. It was serious. I think I moved here after we broke up.

Do you remember why you broke up?
I didn’t want to live in Canton, Ohio.

Did your early success as a businesswoman hinder the possibility of marriage in New York?
Well, I didn’t know if I had enough energy because I’d be adding another level of and responsibility. Plus, my sister and mother.

In some respects, you were a feminist before the word was much in the language.
I wouldn’t have called myself a feminist, but I felt like it. I had a lot of responsibilities.