Making Room At The Table

Sallie Krawcheck is one of my favorite entrepreneurs I’ve met in 2017, after many years following her career as one of the most senior women on Wall Street. A 2002 Fortune Magazine cover put her face as the hope of trust on Wall Street with a headline: “The Last Honest Analyst.”

Indeed, she was fired in 2008 from Citi because she wanted to bank to reimburse clients for bad investments that were the bank’s fault. Or as she put it in an on stage interview in 2016, “I was fired for being a woman,” because women are more focused on relationships and long-term outcomes than men on Wall Street.

What do you do when you reach the pinnacle of your career– farther than almost any other woman in Wall Street has climbed– and then get fired for doing the thing that made you famous? You start a new company, entirely aimed at women, and built off of those same “female” values that got Krawcheck dismissed five years ago.

That’s Ellevest. It raised a staggering $10 million series seed back in 2015. If that isn’t a record for a female entrepreneur, it’s close. Krawcheck just closed her second round, a $34 million series A.

I sat down with her in San Francisco, just after the round was closed to find out more about the process of raising that money. Krawcheck is one of the most senior and prominent women in the financial world. She has served on the kind of committees that invest in venture funds, for Pete’s sake. I wanted to know what happens when someone as accomplished– and yet still female– as Krawcheck tries to raise money.

Guess what: Even Sallie Krawcheck got mansplained.

The amazing interview is below.

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Sarah Lacy: I want to talk about your experience fundraising. This is C? What round is it?

Sallie Krawcheck: No. I’m trying not to label it.  I’ve been calling it an A/B because the first round that we raised, there were no preferences. It was done on PowerPoint, arguably a seed, but it was large. It was $10 million, so some people call it an A.

SL: Jesus, a $10 million seed? That’s big even for the Valley.

SK: Thank you. It’s with folks I’d known for a long, long time who saw the opportunity. Then we did a convertible. Then we did this round. In a way, it has the characteristics of an A, with preferences. In a way, it has characteristics of a B. We’re a year-plus in and are beginning to see some forecastable and dependable and attractive business results. I call it an A/B.

SL: I feel like you’re this canary in a coal mine, in that you should have a better experience raising money than basically any other female founder, given your career and reputation. Set us a Sallie Krawcheck baseline for what fundraising is like.

SK: It was interesting. The first two were easy. I went to Morningstar, which was a company I’d known for years. The CEO I’d known for years. A group of individuals, East Coast-based, investing backgrounds who I’d known for years. That came together nicely. As we’ve moved on to this later round, it’s no longer friends and family. I’ve had to work to break into a world that I really don’t know.

I really don’t know the venture capital world almost at all.I’ve found it’s been the best of times and the worst of times. I’ve been able to get meetings. I don’t think there’s a meeting I wanted that I wasn’t able to get because of my, “You know this person, this person knows you. You should see her.”

But I got it all. I think I got the women-are-a-niche market. Women won’t invest. This just doesn’t make any sense. You’re too late. I’m like, “Too late?” I don’t know what we’re too late for.

I got mansplained to in certain instances. My favorite, or least favorite, was when I actually had a venture capitalist, brand-name venture capitalist who, in a meeting that was 14 gentlemen and myself, which is fine, and I’m used to it, begin to just tell me all the things I didn’t know.

I don’t know anything about digital marketing. I said, “You’re right. I don’t. However, I’ve hired X, Y, and Z, and here are our already-better-than-the-industry-digital-marketing results.” Then there was a point in which I began to say we’re going to hire financial advisers and planners, and he authoritatively told me I didn’t know what I was doing. I didn’t know how difficult those people would be. I don’t know how tough they are to manage.

I ran Merrill Lynch and Smith Barney. Nobody has run more financial advisers than me.

I was flabbergasted. Did you not read my bio? Did you not listen to me introduce myself? Did you not…

SL: Did you not see me on the cover of “Fortune?”

SK: Did you see me on the cover of Fortune twice? I found myself in a very female way, how do I explain this to him without embarrassing him?

SL: How would you recommend someone do that because that’s a hard position?

SK: I thought about walking out of the room because it was clear that they weren’t going to invest. You’re sitting there now, and you’re like, “Now it’s just a matter of getting me out of here because you are wasting my time, and I am wasting your time. How do we wrap this thing up fast?”

I just stated the fact. I ran Merrill Lynch and Smith Barney so I believe I know more about this than anybody else. The meeting just ended from there.

No, I didn’t walk out of the room because you and I both know what happens if you storm out of the room. Then everybody knows you stormed out of the room, and it’s not just them you stormed out of the room on. It’s everybody they talk to for the next month.

“Her ego is insane. Can you believe I think she was crying? She’s been crying. Probably on her period.”

SL: When you say venture capital is different, in what ways do you think it’s different? One of the reasons I liked covering venture capital versus other parts of finance is it’s very individualistic. You have a handful of guys who are controlling what companies get developed, which ones don’t.

I think the things in my early 20s that enthralled me as a journalist covering this industry have become horrific as a woman now in my 40s looking at “Why do we have major problems in this industry?” I’m just curious compared to other parts of the finance world.

SK: You know there are such parallels with my time on Wall Street and with the businesses of Wall Street on the East coast, which is that mostly white males control vast sums of other people’s money in which they choose winners and losers, venture capital, which startups to fund.

Which products do we put resources behind? For which they have provided those investors with mediocre returns at best. If you look at venture capital returns over any period of time, you’re just as well off investing in the public markets with a lot less energy and effort.

If you look at Wall Street returns over time, they’ve been disastrous. Yet, despite all the research that demonstrates that greater diversity will improve these results, you’ve seen the First Round research that says startups with women in leadership positions have 63 percent better returns. That’s a lot.

Over on Wall Street, their research departments are publishing research about how gender diversity is a great way to invest because these companies outperform. Despite this, these two businesses continue to be as non-diverse as anything you can find on the planet. In fact, Wall Street diversity has gone backwards since the crisis.

SL: Silicon Valley has gone backwards since the dot com bubble.

SK: It is not unusual that industries that go through crises circle the wagons and become less diverse. I was never in a meeting where someone said, “Oh my gosh, fire the people of color and the women,” but what I saw a lot of was, “You know I would love to put Suzy or Jose in that job, but we need someone we can trust.” He happens to look, talk, walk, and act just like me. That’s what happens.

SL: This is what drives me insane is everyone in the Valley will tell you how data-driven they are. This was Sheryl Sandberg’s contention in “Lean In”. She was like, “If I paint a data picture of why this should change,” and it hasn’t changed at Facebook. It hasn’t changed in the Valley generally.

SK: Because the “How much better it could be” is a theoretical construct as opposed to the here and now of, “Hey, I’m working with people I like, I’m making money, I’m on top of the world.”

In theory, we could get better returns if…But that means making my life less enjoyable, less easy, and so I’m not going to do it. I think that is the challenge. That it is just theoretical as opposed to you get to live two parallel universes at one point in time.

But here’s the interesting thing. Industries that present themselves as being more meritocratic have less diversity than industries that are not. When it comes to regular old companies, the way I thought about it is they let their middle managers manage. Then they judge them on the results. If you’re a middle manager who hires once or twice a year, you don’t know how to do it. You just default to he’s a cultural fit, which means he’s just like me, doesn’t challenge me and we were in the same fraternity.

SL: Right. I don’t have to do any work to understand his point of view, which means the point of view from this company is necessarily narrow.

SK: That’s right.

SL: Tell me about Rethink Impact, how you got in touch with them, and what was the dynamic like raising money.

SK: It was actually interesting because I had the happy circumstance of after a few of these early meetings, I thought, “You know what? I am now going to be very intentional about the investors that we want to have, that we want to partner with in our company.”

These investors going to matter. Some of them are going to be on the board. Some of them are going to want to build companies for the long term. Some are going to want to get a payout very quickly. We want to build a company for the long term. I need to sit back and actually be very thoughtful about this.

I, for some period of time, had been doing searches on the Internet for firms that invest in women-owned businesses. Sadly, all of them were small. Oh my gosh, here’s an amazing one, and they’ve got two million dollars that they’re investing, or three million dollars, or five million dollars. I just had given up.

A friend of mine mentioned to me, “Have you heard about Rethink Impact?” I hadn’t heard about them at all, Googled them, and said, “Son of a gun, you know, these individuals have raised $120 plus million, in part through UBS, which is no easy feat.” Having run Smith Barney and Merrill Lynch going in to raise money from financial advisers is no easy feat. This is badass. I’ve got to find them.

Was trying to work my way to them, and actually by coincidence, came out to Silicon Valley. Heidi Patel, who is a partner there, ended up in a different meeting for the values-based venture capital fund. Beautiful music began to play when Heidi and I met. We met the managing partner, Jenny Abramson, and it just made sense right away.  I believe we may be the largest of the investments they’ve done so far. It was just beautiful.

Who else do we want in the round? I did what the research is beginning to tell us to do, which is before I fell asleep one evening, I thought, and thought, and thought, and thought about if I could have anybody, who would I want? I went through some names in my head and fell asleep at 3:30 in the morning, woke up and said “Penny Pritzker, the former Secretary of Commerce.”

She’s done great things for women. She’s gone back to her investing business. They build long-term companies. Would you believe two days later, I am sitting down with Penny. I reached out to her, and she said, “That sounds really interesting. Come meet with me.”

The final one was Salesforce who’d launched a values-based fund. Those were really the three that were the big three in our round. I was fortunate.

SL: You already had Venus Williams as an investor. I love that you go around just collecting badass women. I feel like Beyoncé needs to lead your next round.

SK: So do I. Do you know her? Do you?

SL: I don’t. You’ve asked me this before.

SK: I know. I ask everybody.

In fact, we were with Venus the other day and were working on some videos with some of our investors. The woman who was doing Venus’ hair apparently does Beyoncé’s hair too. I couldn’t figure out how to work it in. “Hello, hairdresser to Beyoncé… Do you think Beyoncé would want to invest in Ellevest?”

I was trying to think how do I do this, and I completely chickened out.

She closed the gender gap and she did it when she was young. Yeah, I go around, collect these powerful women, and say, “You need to be a part of what we’re doing.”

SL: How is the business itself going?

SK: Great, and it keeps me up every single night. Today, we’ve got tens of thousands of women in our community. We’ve got thousands of women investing tens of millions of dollars with us, which is not Vanguard, but is a lot. Going back and looking at the old regulatory filings for the other digital advisers, we believe we’re the one fastest, that our initial growth has been faster than the others. What’s particularly great about it is that, first of all, everybody told us it wouldn’t work, and everybody told us women wouldn’t invest online.

SL: Why? Why would women not invest online?

SK: Because they need a person to help them, because they’re too risk-adverse, and because overcoming that has got to be an interpersonal communication, all these perceptions about, and sometimes incorrect perceptions around women and money.

What we’re trying to accomplish is even harder than what the other digital advisers have because the first digital advisers implicitly more targeted toward men. Essentially the value proposition was we can do it cheaper for you. By doing it online, we can provide you with a diversified investment portfolio cheaper than those guys.

For us, it’s more we want you to convert cash into an investment. That’s a very different decision process. Assets you thought of as safe, we want you to invest them in a diversified investment portfolio, which we believe is not as risky as you may think. That’s just a different decision process.

The other great thing about it, and the reason we actually raised money now even though we were fine with funding, is because they’re asking us do to more. What we’re hearing from them is Ellevest is talking to me, speaking to me, and so I’d love to do more with you besides just invest. I’d like to plan with you. I’d like some advisory. I’d like other products. “Can you be part of my life?” which is really exciting.

SL: I am totally part of the problem. I’m in my 40s. I have two kids. I have a house. I had a long career. I don’t invest in anything. I literally have money sitting. I have it in expired 401(k)s that I haven’t even moved. Anything you would think about from my financial life is in such tatters and disarray, but I don’t think it’s because I’m risk averse. It’s because I have so much other shit going on.

SK: You’re busy.

SK: Like most women, I’m taking care of all of that, and not thinking about my needs.

SK: Let me add some reasons to it. Because if you have thought about it, you’ve thought, “That feels like so much work. I couldn’t possibly.” If you have made an attempt to do something about it, you end up with one of the 86 percent of financial advisers who are men and they are, on average, in their late 50s, early 60s. You’re sitting there with your dad, and he’s using jargon that you don’t understand. He’s talking about alpha, beta, and standard deviation, which makes us feel like idiots.

The guys invest right through terms they don’t understand, and we don’t. He’s asking you your risk tolerance, and you’re like, “Dude, I have no idea.” Actually, the research shows you do have no idea, and neither does the guy. You’re like, “I’ll get back to you.” Maybe he’ll give you a book on investing, or maybe you’ll go buy one. You’ll say, “For sure I’m going to get to it.” Guess what?

SL: Years go by.

SK: Doing laundry is more interesting. That’s why when we started Ellevest it wasn’t just, “We’re going to market to women,” which everybody’s done. “We’ve got to change the underlying product. We have to radically rethink this.”

This experience can take you as little as 15 minutes. We’ve seen people go through it in 12. Rather than “Do you want a mutual fund or an ETF?” Sarah, it’s more, “What are your goals in life?” You want to retire? Click. Do you want to start a business? Click. Do you want to buy a house? Click. Do you want to travel around the world? What are your goals?”

We have taken in information about you, and so we calculate out what you can afford to do, taking into account, as only we do, that you live longer, your salary peaks sooner, you take more career breaks. We say, “You can do this. You can’t do this. You can do this.” You look at it, and you say, “Actually, well, what if I…?” This is where we have some patents pending.

“Well, what if I retire later?” “What if I get a condo, instead of a house?” You make tradeoffs. We put together the most highly customized investment portfolio out there for you. We’re a fiduciary, so we choose ETFs, not you. Our goal is to get you to what you want to accomplish in the vast majority of markets.

If you fall off track, “Damn, I really want to start that business in two years,” but the market went down more than we expected or you didn’t make your monthly deposits, we reach out to you. “Hey, Sarah, lady, you need to deposit. You’re off track. You’ve got to deposit 200 bucks or start your business three months later.” Click, done. You can see the big difference.

You’re not watching Cramer and keeping this stock versus that stock. We cut out all that middle stuff and do it for you in a very time-efficient manner. You should come over to us at this moment.

There’s stories now about women who can’t afford to keep up their own homes.

SL: I’m shocked at how obnoxious most financial management commercials are. There’s one where it’s a dad and a son. They’re both mansplaining smugly to each other what they don’t understand. I watch that and I’m like, “Why would I want to do that?”There’s one now. I can’t even remember what firm it is. It’s this smug guy who’s sitting down and talking to people about retirement. He’s like, “What do you want to do?” They’re like, “I thought this was a meeting about finance.” He’s like, “It’s about you.” He’s so obnoxious.

The woman who said she wants to run with the bulls. “I hope you’re fast.” This is what they’re putting forward in a commercial.

SK: It’s even worse, because most of the large firms have women in investing programs. All of them involve marketing only. None of them involve rethinking the underlying product. The one I heard about a few months ago is, “You come to this event. We’ll get facials and talk about investing.” Women love facials, but come on. Come on. Back in the day it was, “Don’t buy shoes. Invest in the stock market instead.” This sense of mansplaining investing to women, “We’re not going to be interested if they don’t think we look pretty,” drives me crazy.

SL: Getting back to venture capital, I’ve started talking to people in family offices who think the asset class may be doomed. It has been a decade of excess. The returns are not there. Everyone keeps hoping for this reckoning, and yet now you have Softbank with this massive$100 billion fund, they could give every unicorn half a billion dollars and extend this non-reckoning for another five years.

To me, I look at it, and I don’t see this changing, in terms of what the industry looks like, what returns are, money going out versus money coming in.

What happens in 10 years to venture capital?

SK: Venture capital can bring value. How else if you’re a small company startup can you become a very, very valuable type of company? Crowdfunding is coming along. I doubt it’ll close that gap. Does that mean that all that money needs to be there?

As I look around, my friends who are entrepreneurs — and you have way more than I do — even the firms and people who have invested in us, every venture capital firm has the same pitch, which is, “We’re bringing money, but we bring so much more. We’re going to open our network to you. We’re going to help you hire. We’ve seen X, Y, Z before. We have this executive in residence who…”

Then it doesn’t happen. For some it does.

I don’t know that it has to all go away, but is there a way to separate out the good from the bad, the good return from the bad returns, the drivers of returns?

You and I were talking about this earlier. The LPs better step up. I’ve been on investment committees, and they seem to let this stuff ride. They are so bedazzled by, “We’re going to be in so-and-so, BSD’s fund. They let us in. They let us in.”

Venture capital seems to have spun this magical view that, “You’ve got to be in, because the return’s around the corner. Did I mention I invest in Facebook when Mark was in college?” Everybody trots out those one story, and they don’t they don’t tell you about the 99 others that failed. Somehow those stories are still working. At some point, if and when the LPs say, “Wait a minute, we haven’t been able to spend X amount of dollars because you guys have underperformed,” that’s when the change starts to happen.

SL: I thought it was interesting in the whole debacle with Binary Capital, it’s one of the first times that I can remember that the case really got pressed to the LPs. Usually LPs sit in the background, hiding, and they like it that way. It was really one of the first times it was like, “No, what are you guys going to do about this?” They actually felt the heat, and they were like, “How did we end up in this situation?”

SK: Me, too. It’s good. It’s good. Money is power. That’s Ellevest’s whole thing. Money is power.

These LPs are bestowing power upon these individuals who are picking winners and losers, and have, some of them, it is now clear, been using that power to sexually harass women. The LPs gifted that to them, and so the LPs have a responsibility.

SL: If we think about how this industry will ever change, in terms of diversity, do you see LPs being part of that? All the same stats we’ve talked about, women outlive men, the amount of wealth that women control in family offices, can women play a role on the LP level of changing to get that power and how it works? Rethink Impact has a lot of badass women behind it. Is that some sort of beacon of hope?

SK: Maybe. It may be easier for the women to take their marbles and fund other women. The investment committees that I’ve been on today remain mostly men. As the universities endowments go out to fill their boards, they look around and say, “OK, so we need to get people with financial experience. Let’s go to Wall Street.”

Remember where we started? Wall Street is mostly men. When I was on an investment committee there were 12 guys and 2 women, or 10 guys and 1 woman. It was hard for the women’s voices to be heard, if they chose to talk about the topic, which is hard to do when it’s 2 of you and 12 of them.

What I saw happen on that investment committee, when the other woman spoke, they would roll right over her every single time. Every single time. In fact, it was fascinating, because — I won’t call him a gentleman — one man on this committee, whom I know socially and think is a delight socially, would get into the meeting and would be so rude to the other woman it almost brought tears to my eyes. If you want to have a gender balance all the way back there, how do you then drive the gender balance through the whole system? It’s difficult.

SL: You need a parallel system.

SK: I’m beginning to think that will be a way, that a few things are going on. Crowdfunding is now becoming a thing, and women do better in crowdfunding than men do. For broad swathes of women, that can be another source of capital for them that can help get their businesses off the ground. Then as some institutions recognize the arbitrage of investing behind women, or some folks who have track records are ready to raise funds, then perhaps we can bring that up. That might be great. More capital, different capital, mission-based capital. Maybe that’s a very good thing, as opposed to trying to change X, Y, Z bro venture capital fund.

SL: In general, I’m more optimistic about the future. I think we are at this tipping point in a lot of things, which surprises people, because a lot of people think I’m so down on the Silicon Valley. In some ways, I am.

SK: I thank God for social. Thank God for social. When I was on Wall Street. Your only choice, you go to HR who was ineffectual at the time, and then you’d have to go home. Then you’d tell some of your friends, and everybody would commiserate with you, and you didn’t have a job.

If you looked at how Susan Fowler used social to get her word out even beyond what Ellen Pao was able to do. Now Ellen’s coming back and retelling her story. It gives us the opportunity for all of us to come together, express outrage, and drive real changes as we see in places like finance.

SL: They’re heroes. This is what’s great because for a long time, you were trapped between what is my conscience telling me to do and what is right. Possibly, what’s the role model I want to be for my kids? What do I believe versus my career will be over in retaliation?

SK: I need money. I’m working for a reason.

SL: What I think is so great about Susan, but in particular Ellen because her story didn’t start this way, is that they’ve now become heroes. Their profile is bigger, and they have had more opportunities as a result of coming forward.

SK: Pull back: So has Monica Lewinsky, and so has Gretchen Carlson. You’re seeing this change. It’s not just Silicon Valley based. It’s the ability for all of us to communicate directly with each other and gather people to a cause. That is a real difference.

SL: When I first moved here, women of my generation or older, they were fine being the only woman in the room. They didn’t necessarily want to be in a room “for women.” That’s really changed.

SK: When I was working on Wall Street, your only choice was I’m the only woman in the room, I’m not in the room. I’ve thought a lot about the queen bee. I was queen bee’d. I was queen freaking bee’d in one of my jobs by a woman who was, “I’m helping you. I’m helping you.” I thought of her in a maternal way, and then realized very dramatically when she was across the table from me when I got fired, she was not helping me at all.

It made sense. It might not have made sense in terms of being a good person, but it made economic sense because if there’s only room for one woman and someone else is coming up and has better results than you do, if you want to keep your job, you got to cut them off at the knees. That’s how they kept us small by having us accept the fact there was only one woman in the room rather than, “Wait, the table can actually grow.” We can have half the women in a room. We can have X percent people of color. There are all kind of things we can do. The table can grow.

SL: Do you think things are better?

SK: Continue that sentence. It depends on where. Depends on where. Corporate America, there’s so much data that shows they’re not. Corporate America’s gone sideways. My old industry has gone backwards. Women CEOs, the second we celebrated earlier this summer that there’s the most female CEOs, blah, blah, blah, everybody started to fall like flies.

Marissa fell, the Avon lady, one after the other. Staples went private. One after the other, they started dropping like flies, and we are going backwards. Women are not receiving more venture capital dollars.

Everywhere you look, it is not better with the exception, or with the caveat, that it feels like there’s an underlying shift that’s occurring. Tectonic plates are moving, and we just haven’t had the earthquake yet. That what we need is in place for this next big move that we probably couldn’t have without social, without all the information we have, without the work that you’re doing, without the work that I’m doing. That’s why I founded Ellevest.

When I looked and said, “I’m not an entrepreneur. I don’t know this world.” When I looked around and said, “I’m young enough that I got a big thing left in me. I am a woman. I’ve had certainly some ups and downs, but all in all, I’ve been so incredibly fortunate. How can I, if you’re going to use the term, engage my only-ness? What can I do to have an impact?

It’s closing the gap we didn’t even know existed, which is the gender-investment gap, which is if the women of this part of the world had another million dollars over the course of their lives, which is what many of them have by investing more, that makes a big difference. For all of us who built platforms, have means to begin working away at this, we can have an impact that we couldn’t have had 5 and 10 years ago.

SL: Every single battle, whether it’s reproductive rights, whether it’s income equality, whether it’s anything, it’s all about economic self-sufficiency.

SK: Money is power. It’s on our website, Ellevest. Money is power. Society has not allowed us to articulate this really because it’s crass, and it’s tacky. Think about interpersonal relationships. You’ll have sex so much sooner with somebody than you do talk about money. It would be tacky to talk about money on the third date, but it is not tacky to have sex on the third date. I don’t know what date people are having sex on. I’ve been married for so long. What date do you have sex on now?

SL: I don’t know either

SK: Can you imagine, you’re taking off your clothes, and you say, “How much do you make?” You’d be like, “Oh!”

SL: Anything else I didn’t ask you? Anything fascinating, words of wisdom, advice for women, VC horror stories, more VCs who didn’t know who you were?

SK: This is advice everyone out there knows. You just have to have a lot of lines in the water. You have to use every connection you’ve got. Something you think won’t turn into anything, it surprises the living daylights out of you. The individual who they’ve been courting, and you’ve been courting them for three years, disappears. You’re wasting time everywhere you go. You just don’t know what time you’re wasting. Everything is low-probability, and everything has to be treated as low-probability up until the moment that it pops for you and you’ve got your round come together.

SL: It’s like looking for your keys. It’s always in the last place you look, but you have no idea what the last place you’re going to look is.

SK: For sure. Then it seems so easy in hindsight, but I can’t tell you the number of nights I sat up and are we going to get there if so-and-so does this, if so-and-so does that, if so-and-so falls away, de-de-de-de-de-de. You’re just herding these cats to do it. That’s what I tell my kids about opportunities in life. You just go for a whole bunch of low-probability things, and only one has to fit.