Doing the Most is a special series about ambition — how we define it, harness it, and conquer it.
Before Sallie Krawcheck founded Ellevest, an investment platform with financial tools tailored to women, she was one of the most senior women on Wall Street. She’s also one of the toughest, having been fired very publicly twice — first from her job as CEO of Citigroup’s wealth-management business, and the second time from her job as president of her division at Bank of America. (Fortune also famously called her “the last honest analyst.”) In 2016, she founded Ellevest with a mission to close the gender investment gap (women are less likely than men to invest their money in the stock market, which means they miss crucial opportunities to grow their savings). Here, she talks about dealing with bad bosses, being labeled “attention-seeking,” and why anger helps her get through multiple red-eye flights per week.
What made you start thinking of yourself as ambitious?
I think I knew it from birth. I’m the second of four, and I wanted to outdo my older brother from a really young age. Then I went to an all-girls school in Charleston, South Carolina, and got severely bullied. I had glasses, braces, corrective shoes, and a truly unfortunate Dorothy Hamill haircut, and I was mocked and shunned and I ate lunch by myself. My mother saw that and pulled me out and sent me to a different school, and right away I went from getting C’s to A’s. Ever since that time, I think I’ve always had a sense of, “Watch me go. I’m going to show them.”
You struggled to find your career niche at first — you’ve mentioned feeling a little lost in your 20s. How did you figure it out?
I was in investment banking in my 20s, and I wasn’t particularly good at it. I think what kept me going was partly ambition, and also insecurity. I wasn’t going to go back to my hometown to those girls who had bullied me and say, “Yeah, I went to New York, but it just didn’t work out.” It wasn’t until I was almost 30 that I realized I wanted to be an equity-research analyst. It took me eight years to get to the point where I felt like my skillset and my job were aligned. Within a year of becoming a research analyst, I was ranked number one. After that, my career didn’t feel so diffused anymore. It felt targeted and straightforward, and I could just go, go, go.
You also had young children by that time. Did that shape your ambitions
in any way?
I think it made me better, although I didn’t realize it at the time. My male colleagues would work all hours, whereas I would work and then go home to play with my kids, feed them, and give them a bath. At the time, I worried it was a detriment, even though I loved my kids and wanted to spend time with them. But now, the research says that your brain does some of its best problem-solving while you’re taking a break. My most creative research often happened after I’d played with the baby. Once I took my mind off things, I’d be like, “Oh, I know! I need to do a multiple regressions over time using PRISMA data to determine the profitability margins of each of the lines of business for the bank.” So in that sense, I think the kids actually helped me early in my career.
You’ve dealt with a lot of pushback in your work environments. How did you handle it?
I’ve gotten pushback all my life. My boyfriend right after college had an ex-girlfriend who tried to get him to break up with me by telling him that I was ambitious and that was an unattractive characteristic. He told me that and I was like, “Yes, and?” Later, when I was promoted to director of research, a number of the analysts quit because they didn’t want to work for a young woman. It was terrible. One of the analysts had a fit on the trading floor in front of the traders and walked out. It was deeply embarrassing. But there was nothing I could do. It’s not like I was going to say, “I became director of research, but then I gave up because people were mean to me.”
It’s one thing to get pushback from people who work for you, but it’s even worse when it comes from bosses. What was that like?
When I was in a senior-level Wall Street position, I remember getting criticism from a boss about my ambition. This was right after the financial crisis. I walked into my performance review and was told that they only had two pieces of feedback for me, and they were both negative. The first was that my work ethic was too strong and it was intimidating and off-putting to the other folks on the leadership team. And the second was that my profile was too high. I think I had to pick my jaw up off the table. I said, “Wait a second. My business results are great. And we’re coming out of the financial crisis and you’re criticizing me for working too hard?”
But the part about my profile being too high — that really stung. A uniquely painful way to put down a female is to say that she’s looking for attention. We’re taught to be self-deprecating, and the research tells us that when women are seen as wanting power or attention, there’s a backlash against them. But not so for me. I remember saying to the person who gave me this performance review, “I haven’t done a single interview at this company that hasn’t been requested by our head of PR. If my profile is high, it’s because the business is doing well and I stand out because I’m a woman. I don’t know how to reverse that.” And this individual told me, “Well, that’s your problem.”
You’ve also been fired twice, very publicly. Did you ever have a moment of worrying you wouldn’t be able to make a comeback?
Nope, absolutely not. Especially the first time, when I felt like I got fired for the right reason. I was the only senior executive who successfully fought to return money to clients after the downturn [in 2008]. I knew that if I got that money returned, of course I was going to get fired. But I felt really, really solid about it. I thought, “What would I want my kids to see me do?”
The second time I got fired was different. I got reorganized out of Bank of America, and that time, I did have a moment. I was standing in my living room the day after I got fired, and I thought to myself, “What if I don’t come back? What if I don’t make it?” But then, just a minute later, I was like, “No, because I’m just not going to give up until I do. That’s it. Move on.” I think I am the only woman who’s been fired twice on the front page of the Wall Street Journal and just keeps coming back. I would also say that my success and my getting pushed out are two sides of the same coin. I’ve come to realize that there are a thousand opportunities to be successful every week, every day, every month. The way success gets written about, it seems so linear. But no.
When you’re totally exhausted because you’re flying all over the place and growing your business, what do you do?
I hold two competing thoughts in my head all the time. One is that I’m just so frustrated and angry that we’ve built a society where women have less money than men. I’m energized by that anger, and driven by it. That’s half of my brain. The other half is like, how fun is this? Seriously! I walk through airports with my Ellevest bag and young women stop me and say, “Do you work at Ellevest? You’re changing my life.” That happens all the time, and it’s amazing. And to be able to build a company where I want to work, and where I would have liked to work when I was younger — it’s so much fun. So I’m pissed off and grateful, simultaneously, and I’m ignited by that. I had one week, two months ago, when I took two red-eyes in the same week because I just didn’t want to wait an extra day for the next flight. I wanted to take that red-eye and get off that plane and get back to it.
Also, I’ve learned I need to exercise. When I was younger, I didn’t, but now I do and it helps. And I need to cook. My way of fueling myself back up is to go in the kitchen for half a day. And I have a glass of wine every single night, whether I need it or not. It enables me to just take it down a notch. I can’t remember a time when I got to the point where I was like, “Oh God, get me out of here.”
Lots of people really want to succeed, but very few of them are at your level. What makes the difference?
I don’t know. I think it is some degree of hard work, for sure. There’s also some degree of luck. And I don’t mean like, “Oh gosh, they called me and said, ‘Would you be CEO?’ And I said, ‘Who, me?’” We’ve been socialized to act like that, but nothing’s ever dropped in my lap that I can remember. By luck, I mean that I never worked for a Charlie Rose or a Matt Lauer or tried to make a movie with a Harvey Weinstein. Also, I never worked for a Todd. Who’s Todd? Todd is that middle manager who’s so terrific and nice and has a daughter and talks about unconscious-bias training classes but, still, he just never promotes a woman. Some of the women in my business-school class got caught working for predators, but more of them got caught working for a Todd. It’s just luck that I didn’t.