Listen in now, or read on for the transcript of our conversation:

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Amanda Steinberg, author of Worth It- Your Life, Your Money, Your Terms and founder of DailyWorth and WorthFM, shares her journey of finding her identity and increasing her net worth. Amanda discusses some of the obstacles that keep women from accumulating wealth, and how to overcome them. She also addresses the need for women to invest their money in people and causes that they believe in and the social impact that investing can create.

In this episode, you’ll discover: 

  • How Amanda’s mother supported her in finding her own identity (3:00)
  • Why Amanda felt she needed to leave her marriage (8:00)
  • What led Amanda to address financial services specifically for women (14:00)   
  • The perception of women in the financial services industry (15:00)  
  • A problem that Amanda found with female investors (19:00)  
  • Why women need to invest money in startups and political campaigns (22:00)  
  • What an angel investing network is and how to get involved with one (25:30)  
  • The potential pitfalls of the free market economy (29:00)  
  • How to build in protections against bias in corporations (32:00)  
  • The underlying fear that keeps people from supporting diversity efforts (34:50)   
  • The coming transfer of wealth to women (37:00) 
  • How women can shift their financial behaviors regardless of their net worth (38:50)
  • A mindset shift that has helped Amanda grow her following and community (41:00)

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Listen in now, or read on for the transcript of our conversation:

JENNIFER BROWN: Welcome to The Will to Change, I’m Jennifer Brown.

My guest today is Amanda Steinberg. Amanda launched DailyWorth in 2009 to bring a fresh voice and an outsider’s perspective to personal finance. Today, DailyWorth’s newsletter reaches more than one million subscribers.

In 2015, she started the digital investing service WorthFM, which received front-page coverage in the New York Times business section.

Oprah selected her for the exclusive Super Soul 100. Fast Company named her one of 2016’s most creative people in business. Forbes named her one of 21 new American money masters.

Amanda has appeared on Good Morning America, The Today Show, CNN, MSNBC, and is the author of Worth It: Your Life, Your Money, Your Terms.

Amanda, welcome to The Will to Change.

AMANDA STEINBERG: Jen, it’s so great to be here.

JENNIFER BROWN: I’m so excited you’re on.

We always start with a diversity story, and I know from learning about your childhood, your mother in particular, that you had some really interesting relationships with gender norms as a girl growing up. You also are one of the fortunate women that I meet who have incredibly strong female role models from a business perspective in your family.

Would you take us back to realizing something was different for you in terms of the expectations? Also, tell us a little bit about your mom, if you would.

AMANDA STEINBERG: Yes, gladly. I guess I can just summarize it: As a kid, I liked boy things, and I didn’t like girl things. I wanted Transformers, G.I. Joe dolls and to play Little League baseball.

In 1985 suburban Philadelphia, I was an anomaly. At least I was an anomaly that spoke up about it. Maybe there were lots of other little girls who felt the same way who didn’t feel as comfortable doing so.

My parents separated when I was three, and my mom definitely went through a long, dark phase in terms of struggling to figure out who she was going to be as an independent woman who never planned to be independent. The thing I always really cherish about my mom was that she always supported whomever I wanted to be.

JENNIFER BROWN: That’s incredible. Fast forward to your early adulthood and your first marriage. Tell us about how you were still living a life that didn’t quite feel authentic to you in terms of your career, your marriage, and what the gender dynamics were in all of that, along with expectations. Tell us how it took you to a very dark place before you had to strongly reinvent.

AMANDA STEINBERG: Yes, it’s funny. Even though I was raised by a pretty feminist mother and I was allowed to be whomever I felt like being — whatever that looked like — social pressures are way more intense than even individual will or family permissiveness.

Despite my somewhat more masculine interests as a child, the other thing that made me feel really different was my level of ambition. I would look around at the world, I would look around at all of the poverty and suffering and messages I would receive through the media around what was going on in more impoverished places, and I had the ridiculous notion from the time I was five that I could do something about that.

I’ve never seen limits, and I don’t see risk. It’s just part of my brain structure. Which sounds interesting, it also gets me into massive trouble and major hot water constantly. I’m an expert at digging myself into giant holes that I then have to pull myself out of.

It’s really scary when you’re 20 years old, you realize that you have this power to make a lot of money and to build businesses, which I did at a really young age. I was worried I’d become the lonely old lady with cats — which is really funny because I have.

JENNIFER BROWN: Nothing wrong with that.

AMANDA STEINBERG: That’s the joke. There is absolutely nothing wrong with that. Just because you’re alone, it does not mean you are lonely, and all those distinctions we learn as adults.

By 22, I decided, “I had better get married and have kids or else I’m going to be miserable.” There was this equation of causality that even intellectually we know isn’t true, and yet those damn social pressure are so harsh.


AMANDA STEINBERG: I got married at a young age, had kids at a young age, bought a house at a young age. My ambition translated into my personal life, and I got very good at not only earning money, but earning all those attributes of a, quote, unquote, successful life. That sent me into a really dark place because I had a massive identity conflict between what it was I really wanted versus making other people happy. And why was I so damn tired and out of control?

JENNIFER BROWN: Yes. I’m sure. Looking back, you’d probably describe it as a really depressed time. You were still taking a lot of risks. You dug yourself into some financially tough places.


JENNIFER BROWN: Tell us a little bit about your first efforts to be a businesswoman and what you wish you’d known. Where did your appetite for risk really serve you, and where did it get in the way? What was the gender dynamic you were experiencing or maybe fighting against at that point?

AMANDA STEINBERG: Well, my risk tolerance has always served me in that I’ve been able to put my mind to things and take the necessary risks. Whether it’s building a consulting agency as a software programmer for the first ten years of my career. Whether it’s being able to build the business that I wanted on my own terms so that when I had children, I could work from home and not worry about anybody else’s rules, which was always important to me.

It also came with this massive amount of optimism, “Everything’s going to work out.” The reality is that I bought a house that needed $30,000 for repairs and didn’t understand the investment dynamics of owning a home.

Then my business grew so much in one year that I ended up with a $60,000 tax bill. So there I am, close to $100,000 in debt with a two-year-old and a newborn in my arms. For those of you who have children, you know how exhausting it is. For those of you who don’t, the level of sleep deprivation that comes from babies — especially the amount that mothers typically have to take on for various reasons — compounds all of that. It was a pretty dark couple of years.

JENNIFER BROWN: Tell me about your husband. At the time, maybe he wasn’t the right kind of partner. It’s easy to say. Of course, when you’re in it, it’s hard to see. You really hit a wall in the relationship in terms of how it was supporting you and how you needed to show up in the context of it as well.

AMANDA STEINBERG: Yes. Even though it was always obvious to me, and I expressed it, I think that there is an expectation around how mothers behave in society these days. We can have some ambition, but not too much because that means that you, then, are neglectful of your family.

And I think everyone, including myself, thought that once I had children, some of my ambition would taper off. That didn’t happen. And as a result, I even went to therapy for many years in order to try and change my ambition, change level of things that I was aiming for. That is actually what led me to the most depression. When I would try to modify myself and reduce my goals and stop putting so much pressure on myself to build a successful career, I felt like I was becoming someone that I didn’t recognize.

Eventually, you have to realize, “You are who you are.” And it’s hard to modify.

JENNIFER BROWN: That’s so true. You told me a story about the day you decided that you were going to get divorced. You said to yourself, “I’m going to live my life as who I am.”

AMANDA STEINBERG: I did not have a choice. And I imagine for folks who are gay, who are transsexual, who are all these different types of things where what you are does not fit the norms, there’s a day where you break. You say, “I’ve tried to change, I’ve tried to be something I’m not.” And that is even worse.

Yes, there was a day when I decided I was finally going to become fully independent, no longer part of a marriage, move out, get my own apartment, and stop trying to modify myself.

I drove out into the street, and I remember screaming and crying, “I don’t care what the future of my life looks like, I just know that I have to be who I am, I can’t change.”

JENNIFER BROWN: In your selection of your current life partner, obviously, diametrically opposite choice criteria. Tell us a little bit about him, the role that he plays, and what he has been able to solve for in supporting you that your first relationship really didn’t.

AMANDA STEINBERG: It’s funny, that day when I drove out of my house in my ex-husband’s car so that I could buy my own car so that I could leave, I ran into my current partner at a traffic light. I had known him from grade school and had not seen him since. We’ve been together basically ever since that day at the traffic light. It was literally two seconds.

JENNIFER BROWN: That is so magical, I love that story.

AMANDA STEINBERG: Which is weird because I think five seconds prior I had sworn off all men.

JENNIFER BROWN: Exactly when the universe gives you what you need. They wanted to cut you a break, you had been through enough.

Tell me about him. Is he a feminist? Would he describe himself as a feminist? Would you describe him that way?

AMANDA STEINBERG: He would describe himself as the ultimate feminist. The theme of our relationship is actually a Radiohead song that we love, Lotus Flower, where the chorus is, “I set you free.” That’s been the theme of our relationship, which is amazing because if I feel like I’m trapped, I turn into a nasty, nasty person.


AMANDA STEINBERG: You can’t tell me what to do! It’s so immature, but I see it showing up constantly. We live separately. We live ten blocks from each other. We both have two children from our prior marriages. We only see each other a couple days a week. We are both traveling a lot. We live separate lives together, which is exactly what both of us needs and wants. I did not think that that was possible for real.

JENNIFER BROWN: Right. Nobody does that, or at least we don’t think they do. And it’s certainly not socially sanctioned.

AMANDA STEINBERG: Right. For sure.

JENNIFER BROWN: Yes. That’s so cool. How did he get so cool? How would you summarize his journey to waking up, being woke, like he is?

AMANDA STEINBERG: I think he’s just always been that way. I don’t know. Like me, he didn’t fit norms, knew the feeling of feeling really lonely at times in his life. He was always unconventional, creative, artistic, didn’t like sports — stuff like that. So he was just very familiar and open to the fact that gender does not have to be a precursor to anything specific about who you are, how you act, your roles in relations, who earns money, et cetera, et cetera, et cetera.

JENNIFER BROWN: That’s so fortunate. Did you read Lean In?

AMANDA STEINBERG: I did. I was one of its first reads, actually. I got an early copy.

JENNIFER BROWN: That’s so exciting. Wow. Do you feel super radical compared to what was talked about in that book? Could you relate? Did you think it went far enough? What were your reactions?

AMANDA STEINBERG: I think that Lean In was intended for a mass audience of women, as opposed to people like me who are anomalies, we’re outliers. It was fantastic because it really brought in the conversation of giving women permission to be ambitious. “Ambitious” is still a bad word for many women.


AMANDA STEINBERG: Because we’re afraid that our ambition makes us unattractive and unwanted. In some cases, it does make us unattractive and unwanted to a certain segment, but there are plenty of people out there who are far more gender fluid these days. Thank God for that. We are speaking up a lot more now, and gender is becoming — slowly, but surely — less of a determinant.

JENNIFER BROWN: Slowly. My goodness, you are right about that. We’ll talk about all of the things in the news later on.

I want to change gears a little bit. You did your time in financial services, right? Now you’re the money guru for women, and such an important asset to our community and to the conversation. I really appreciate what you’re doing for so many women — demystifying the process, educating them, making sure they’re saving and protecting themselves in a way that maybe you didn’t know to do early in your days. You can see how your mission has come full circle, which is really cool.

So you were in the institution, in the financial services world, and you were noticing so much bad behavior. I don’t think there’s enough time in the world to catalog all of the stories that you were sharing with me. What was that like? When did you get fed up and realize, “This system is not worth this energy, and I’ve got to build it anew. I’ve got to build a parallel world where I can really address what I’m seeing here”?

AMANDA STEINBERG: The financial services world that I’ve been living in — I’ve had DailyWorth for eight years now. For the first six years, DailyWorth was a media company that sold advertising.

What was interesting was how the heads of financial services institutions and those who are responsible for marketing at the deepest strategic levels saw women as an ideal, quote, unquote, target — I love the language of advertising, target, quality target — for the future, but recognized that women were not engaged in financial services nearly as much as men who would be on a website like MarketWatch or Yahoo! Finance, which are really, really heavily read by men.

There were multiple stages of how furious and frustrated I became with the industry at large and their approach to new markets and perceptions of women. But it really came down to the fact that in 2014, DailyWorth‘s advertising revenue, which was in the multi millions, started to plateau. And I could see it was going to start going down because the perception was that women aren’t really interested in money, and when they do contact financial services institutions, they ask too many questions, and therefore, are not profitable to serve.

I’ll give you a little bit more context so you know what I’m talking about. DailyWorth is a daily e-mail about personal finance, and we made most of our revenue by selling advertising to the companies that want to manage your retirement and your investment accounts. So we’ll call them “brokerages” as a broad-sweeping term. There are lots of different types, but for all intents and purposes, we’ll call them brokerages.

I’ve talked to the heads of marketing in probably every brokerage in this country that wants to advertise nationally, because that was all we did for years and years.

And I saw their hesitation that was specifically gender delineated. I knew they weren’t reaching women because most women don’t read financial media, but I didn’t realize there was this conscious bias around women being high-maintenance customers.

That made me turn DailyWorth into Worth Financial, which is now an asset management company. When the advertising revenue started to go down, the board of directors of DailyWorth decided it was time for me to sell DailyWorth because they were nervous that we were going to go out of business as a result of this.

I went around and met with a lot of CEOs and heads of corporate development at these large companies. Instead of hearing them embracing the possibility of women engaging with financial services on a deeper level, most of them actually explicitly said they weren’t interested because they did not see women as profitable customers.

I thought, “This is half of the market, and in order for women to become equal, we need to be able to control and engage with our finances.” There are trillions of dollars flowing into women’s hands. I decided, “I am not going to sell DailyWorth right now. I am turning it into your competitor, and I’m going to serve half of this market very happily, thank you very much.”

JENNIFER BROWN: Yes! I love it. That’s so good. Yay!

You talked about women asking too many questions. When you look at customer service metrics, you can see this. Literally, the time that a rep spends on the phone to answer those questions is not profitable time. It’s so cynical to think that we’re just too expensive.

Interestingly, you thought that women’s propensity to ask too many questions hurts us in terms of playing in the financial world in the way that we really need to. Can you say a little bit more about that?

AMANDA STEINBERG: Yes. Women do need to ask lots of questions, and they’re actually totally right to be asking these questions. I will give you some examples of questions we get over and over again at WorthFM, which is the investment side of our business. “How do I know if my investments are performing? How much do my investments cost? What type of investments am I invested in and why? What type of accounts do I need?”

These are all very, very logical questions, but it becomes a challenge for us as a gender. I realized through two additional conversations that this is still something we as women need to address.

The first thing that happened was when I had been raising money for Worth Financial — venture capital, because we’re not profitable yet, we will be soon, so we’ve needed external capital in order to grow. What I found was that I would talk to women investors, those affluent individuals who can afford to invest in startups, and they, too, would ask so many questions. I would have three different phone calls and meetings with a potential investor, and more often than not, the women would say, “No.” Whereas more often, the men would have one phone call and make a decision, either yes or no. At a much higher rate, I had a lot more success raising money from men than I did from women.

Part of this is because women have not been in control of the finances for most of their lives, so it’s newer to them. Either they weren’t raised to understand it, they inherited it recently, something changed, or what have you.

But then I realized that women asking questions was more of an issue. I was having dinner with the former mayor of Philadelphia. He’s a mentor of mine; I worked for him when I was in high school before he was mayor. And he said, “You know what, Amanda? I think what you’re doing is really important around women and money. When it comes to political fundraising, women would oftentimes ask way more questions and also be far more likely to reject the donation than their male counterparts.”

So on one hand, while it’s totally valid that we need to understand everything about how our investments work, we also need to become more risk-takers as women and put a little more of our capital at risk. That’s why the political field and the business field are still so male dominated — they’re the ones writing the checks. But women have just as much money as men do.

JENNIFER BROWN: That’s so good to hear. You said something beautiful, “Questioning is an avoidance of the power we need to take.”


JENNIFER BROWN: I wrote that down when we prepared for this. If we want the world to be equal, do you have advice for those of us who are really risk averse? Who knows? Maybe because of socialization, maybe you were born that way, thinking back, is there anywhere you learned it? Or do you really think it was hardwired into you? For some of us for whom it’s not hardwired, what do you recommend?

AMANDA STEINBERG: First of all, for those of you who are listening, everybody has a different financial situation. If you have a lot of credit card debt, if you have loans that you don’t understand and you don’t have at least a couple of months in savings, then you shouldn’t be taking a lot of risk. You should be doing what you can in order to pay down that debt, et cetera.

If you are someone who makes multi-six-figures, has at least $500,000 saved, and you feel like you’re on track, those are the ones whom I tell to take an amount of money, maybe a quarter of your liquidity. Let’s say you have $30,000 in cash, maybe take $5,000 of that and put it to work somewhere else. And if you have millions of dollars, it’s all about asking: What percentage of your money can you put at risk that if it disappeared, it wouldn’t make a difference in your life?

It’s vital that we put some of that money to work either in the politics that we believe in or for the startups that we think need to really exist, that capital is very much needed and there’s nowhere else to get it other than from wealthy individuals who are going to take a risk. So women need to put more of that money to work.

The other distinction I’ll give you is there is “excessive” risk, and then there’s “calculated” risk. Understand, all risk is not created equal. As far as the money I’m talking about, there are plenty of people out there for whom losing $25,000 would not make any difference in their long-term life. There are other organizations out there that need that risk as well. And you may lose all of that money. If you are donating to a political campaign, you do lose all that money. But you don’t really lose it because you are creating things in the world that will not exist otherwise, and that’s vital.

JENNIFER BROWN: Vital. And it’s vital that we see more role models of women who are really playing on the big stage, they’re jumping in.

What’s going on in the VC world? That’s one of the big negative narratives that we read about all the time — a stark lack of women investors. What do you think would change that frustrating reality that we keep reading about? It’s probably similar to the lack of diversity that we see in so many big corporations and their top leadership.

AMANDA STEINBERG: I think that there is a grotesque amount of sexism in the industry. And I think that it’s going to take really amazing leaders. I know plenty of male VCs who aren’t slimy bastards, and I know plenty who are. I was once almost drugged. I have been hit on more times than I have fingers and toes to count. It’s not uncommon for a VC to use a pitch meeting from a female founder as a way to try and hit on her. There are articles about this constantly.

Oftentimes, these are really high-profile people, and as female founders, we can’t afford to piss them off, so we’re silent about it. It’s everywhere.

There is a lot of press today about all of these women who have come out against one particular VC, I’ll try and find it right now as I’m talking to you. I’ve seen six people share it, which is good. I didn’t share it because I got scared. I’ve got 20 VC friends, and I may need them in the future. I’m still falling victim to this.

That’s all the more reason for women to step up, write more checks, and become angel investors. Otherwise, it is a horribly, horribly slanted playing field.

JENNIFER BROWN: That’s right. Can you share with our listeners the angel networks? Explain what that kind of investing is. What are the reputable organizations and communities you can get involved in and how does it work?

AMANDA STEINBERG: Absolutely. The way it works is if you make $200,000 per year for the last two years as an individual or $300,000 a year as a household for the last two years, or you have $1 million in net worth, then you are what is called an “accredited” investor. That means that you can buy shares in small, private companies that have the potential to grow and become worth ten times their value through some form of exit in the future.

That is called “angel investing.” It’s not like investing for your retirement, it’s not like a stock portfolio. It’s high-risk investing where you’re either going to lose all of your money or you’re going to make a massive, massive return, and usually not a lot in between.

As a result, most who do angel investing do it for a variety of reasons. Maybe it’s wealth that they would otherwise put forward philanthropically and want to support small businesses, that’s very valuable. It could be those who have enough wealth that they can afford that level of risk and want more diversification. There are also strategic angel investors who follow methods like investing in ten companies, knowing that one of them is likely to be a homerun. They work very methodically to invest in ten companies knowing that one of those is going to be the homerun that’s going to give them the return that far outweighs all ten investments. Those are three ways in which people can angel invest.

I will give you a few names that I’ve had a lot of success with. One is called Investors’ Circle. That’s a national angel investor network that invests in double-bottom-line businesses. One is called Astia. One is called Golden Seeds. You can just look up “angel investor network” and then put your city in. I know of Baltimore Angels, in Philadelphia we have Robin Hood Ventures. There are many popping up at universities. I know the University of Pennsylvania has one. I’m sure Harvard has one. Look for your alumni network. There are tons. Just start Googling.

The other place to go is AngelList, you’ll find a lot of good things going on there.

JENNIFER BROWN: Thank you. I wanted that to be explained. I remember learning all that for the first time, not realizing how easy it is to get involved. We need to show that we’re investors, not just the businesses being invested in — we also need to be that as well.

Did you follow the film, Equity?


JENNIFER BROWN: It was so cool. What were your observations about how that got made or the power of having an all-female director team, writing team, investor team? They literally got all of this investment money from women, often women who had been in financial services.

AMANDA STEINBERG: I just thought, “Wow, there’s a movie about women in financial services.”

JENNIFER BROWN: Wow! Pinch me.

AMANDA STEINBERG: Wow. There’s a movie about women in banking. We haven’t seen that before.

JENNIFER BROWN: Which is so sad. I know.

AMANDA STEINBERG: The progress we look for today.

JENNIFER BROWN: Yes, they’re small crumbs of hope.

AMANDA STEINBERG: Two days ago I went to a luncheon for Travelzoo, which is a publicly traded company, whose board is now 80 percent female. They’re the first one to be 80 percent female. On one hand, “Yay.” On the other hand, “Why is this the first time this is happening?”

JENNIFER BROWN: I know. I know. Why is it such a newsworthy item? I look on with envy at Europe and the fact that they set quotas for women on boards. I think it’s 40 percent in many countries, and they actually achieved it and the sky didn’t fall and the world didn’t end. Somehow, they magically came up with a pipeline of women board members and everything is proceeding along. I don’t know what it is about our country and our history that makes it such a taboo conversation to be having.

AMANDA STEINBERG: Well, this country worships the free markets as gospel. I don’t worship the free markets. I think free markets, left to their own devices, are going to reward the rich and make everybody else poor. But for whatever reason, even really poor folks don’t vote that way, they vote for the free markets. I’m a big fan of regulation, and absolutely think our companies need to be regulated in order for our society to work. But in this country, the religion is the free markets. We’re getting into politics here, which we should probably stay away from for right now.

JENNIFER BROWN: It’s all right. It’s all right.



AMANDA STEINBERG: But it’s a deeply political discussion about beliefs about what makes society better, and I think regulation does a lot of really important things.

JENNIFER BROWN: Yes. And free markets are not exactly free of bias. When we think about those people who are making those decisions, the representation of different kinds of people is not there, but also the decisions that are made are biased. We all are. We carry that around with us every single day.

AMANDA STEINBERG: Everybody has bias.

JENNIFER BROWN: Yes. And it’s unchecked and very unaware — although aware in some cases that, unfortunately, we’ve been seeing in our national leadership as well. Sometimes it is overt bias, and it’s so shocking when you see it. There are many, many more cases of being generally well intended, but not really understanding your level of biased behavior.

AMANDA STEINBERG: We all think bias is bad and wrong and would like to think that we’re all evolved, that we’re color blind, that we’re gender blind.


AMANDA STEINBERG: I imagine you know this more than anyone, but everybody is biased. Remember the Korea expert on BBC whose two children walked in and interrupted? Remember?


AMANDA STEINBERG: I spent the first 24 hours saying, “Did you see the nanny run in?”

JENNIFER BROWN: All of us did.

AMANDA STEINBERG: And it wasn’t the nanny; it was the wife. I thought, “Well, there you have it. I thought it was the nanny.”

JENNIFER BROWN: Meanwhile, she’s this tremendous businesswoman. I don’t remember what she does.

We all do it, women especially because we haven’t seen a lot of role models to challenge that bias. Even those of us who do this work find ourselves jumping to those conclusions. It’s crazy when I find myself doing that. It is shocking.

AMANDA STEINBERG: Either it’s crazy or it’s a part of the human condition that we just have to be accountable for and create scaffolding around.

I teach this a lot in our financial advice. We have all of these archetypes. If you are like me, you are a visionary archetype, meaning that you don’t see risk. We’re not going to change you so that you do see risks. You have to build in certain protections to account for that. I guess that’s where regulation comes in.

JENNIFER BROWN: Yes. And in the corporate world, there are protections against bias. When I work with corporations, I say, “Okay, let’s look at your recruitment practices. Let’s look at the schools you’re looking at. Let’s look at the job description and see where there’s gendered language in the way that you have described the role.” There is such a thing. In fact, there are tech startups right now that you can plug in your job description language or your performance review language, and it will go through and flag all of the gendered terms. It’s really incredible what technology can do now, and it will suggest alternate words.

So if you’re looking for a “coding rock star,” women are actually going to read that and say, “This isn’t going to be a fit for me,” and they may pass on that opportunity. Just an example of some language that women don’t relate to. It can be as small as that.

It can also be looking at who you’re promoting and advancing and who gets involved in talent reviews for that promotion. Do we have diverse slates of people to review, assess, and promote?

People assume a meritocracy. They assume that the right talent is going to rise to the top.

AMANDA STEINBERG: Haven’t already seen that that’s not the case?

JENNIFER BROWN: Well, we have. Yes, we have. I always say, “Diversity is not just going to happen because you’re well intended or you happen to believe in equality.” Even if you talk a big game or if your company wins a lot of awards, in my experience, it has nothing to do with the culture inside the company and the messages people are getting about whether or not they’re welcome.

AMANDA STEINBERG: That alone is a really, really powerful message. I wonder how many executives in really powerful places would accept that. Even with the best intentions, diversity won’t work, it has to be proactively implemented.


AMANDA STEINBERG: I’m curious how many would believe you.

JENNIFER BROWN: I know what you mean. The other interesting power dynamic is that there is an assumption that if I open the door and welcome this and broaden my lens, it is somehow going to jeopardize what I have. I always think of diversity as, “One plus one equals three.” All of these things we talk about. It’s going to make us a better leader. Leading across difference is probably the number-one skill set that we’re going to need for leaders in a very volatile world. And yet, we’ve got to get to the heart of what people feel and sense is being taken away from them if they somehow support this or participate. Some of that is true.


JENNIFER BROWN: When you think about the election, think about what we learned about economic opportunities for certain people. What is changing so fast that it’s endangering the very economic viability of so many people? I don’t have any answers for that, it’s going to continue.

It reminds me of the stance towards diversity which says, “I need to protect what’s mine, and I don’t know what’s on the other side of this diversity conversation. What is it going to mean for me?”

Do you think we’re undergoing a culture shift at the same time in the opposite direction? Do you see signs of hope and change in terms of gender relationships? Maybe it starts with men revisiting — heterosexual men anyway — how they partner and support women in their lives.

Certainly, we see that wealth is changing hands really, really fast. We see female customers, for example, refusing to work with their husband’s wealth advisor because they’ve never been talked to or considered part of the conversation. Suddenly, they’re going to be in charge of all of the buying decisions and all of the wealth, and they’re faced with a largely male financial advisor population, interestingly.

AMANDA STEINBERG: I’ll tell you this: I don’t feel really hopeful right now, but if all the women listening today and more and more women take risks, and we decide to create more of our society in our own vision and start to invest more capital in the more equitable, democratic institutions that we want to be serving us, then, yes, I will have hope.

But we have to see a shift in the way women are distributing capital. Women are inheriting the majority of wealth. Women are inheriting trillions of dollars in this country right now, but we’ve got to put our money where our mouth is.

JENNIFER BROWN: I love that. The whole vision of us hoarding our cash, which of course is rooted in not having ever controlled that before.

AMANDA STEINBERG: We weren’t prepared. We don’t know how to deal with it.


AMANDA STEINBERG: It’s a foreign object. We think, “Oh, God, I don’t want to screw it up.” Of course.


AMANDA STEINBERG: People screw it up sometimes. They do end up poor when they had millions. I’ve seen it multiple times. It does happen. There’s a reason to be somewhat scared, but that’s not a reason not to figure it out.

JENNIFER BROWN: How can our male partners in life and business, our friends, how can they support us to show up differently around our money habits and beliefs?

AMANDA STEINBERG: I think holding their male colleagues and friends accountable to less sexism is huge.

I was sitting at my car dealer the other day. One of the car dealer reps walked up to another with a picture and said, “Look at my new baby boy.” And the other said, “Oh, you had another son. You’re so lucky. Girls are such a pain in the ass.” And I thought, “Wow, that was cute.” How much of that banter goes around? “Boys are low maintenance; girls are high maintenance. You’re so lucky you have sons.” Things like that. Change that conversation, and don’t let even those tiny little quips be acceptable anymore.

JENNIFER BROWN: Right. And every parent I know says, “The boys are so much work, but the girls are a delight.” You hear the opposite all the time, too.

AMANDA STEINBERG: Let’s stop making gender a determinant of children.

JENNIFER BROWN: Yes. Agree. That’s great, Amanda.

One last question: Say a woman does not have the assets to become an angel, although may some day, what can we do in our lives with whatever we have to start to shift our thinking about ourselves, the narrative that we have with ourselves, and also our financial behaviors? What is going to make the most difference?

AMANDA STEINBERG: Well, I wrote a book.

JENNIFER BROWN: Yay! Good segue.

AMANDA STEINBERG: It’s called Worth It, and you can go to Amazon and search for “Worth It, Amanda Steinberg.” I recommend that you read my book. That’s exactly what it’s written to do — to shift your mentality. I promise you, it’s entertaining. It’s not another boring money book. I would have fallen asleep writing it.

JENNIFER BROWN: I can vouch for that. It’s awesome, a great read.

AMANDA STEINBERG: Thank you. And if you want to start proactively managing your money, I also invite you to check out WorthFM.com, which stands for Worth Financial Management. That’s our investment advisory business. It’s all digital. You can sign up online, you never even have to talk to a human, but you can talk to a human. We help you get started really controlling and managing your money.

JENNIFER BROWN: Fabulous. I love your voice on Facebook. I want to tell people where they can find you. You’re so real. You’re one of the most real and accessible human beings, and not afraid to show that you’re flawed.

AMANDA STEINBERG: Because I’m highly flawed.

JENNIFER BROWN: That’s part of what we have to unpack as women, honestly, showing this face to the world that takes so much time on the back end to create and polish. I’m always aware of commenting about how we look on camera or trying to delineate and create this boundary between the mess that we may feel in our daily lives or the chaos with our kids or whatever it is, and then presenting this other thing to the world. You really have successfully and beautifully navigated your truth in all of its glory.

AMANDA STEINBERG: Well, it goes back to that day. You can find me, just search Amanda Steinberg. I have a professional page, too, with one of those blue checkmarks, but I really never post there. So just follow my personal profile.


AMANDA STEINBERG: It all started that day at the traffic light when I gave up on everything I thought I was supposed to be and only embraced what I know that I am. And this magic happened in my life.

Every time I have put myself out there as flawed, I actually get a greater embrace from an even larger community. So it’s totally out of self-interest that I’m authentic, because when I’m authentic, everything in my life works better. I don’t know if that’s true for everyone, but it’s true for me, so I just keep doing it.

JENNIFER BROWN: I love it, and it’s really resonating.

Thank you, Amanda, for your wisdom, your risk-taking, your dedication to empowering women in these really concrete ways. I think my favorite thing you said today is we have got to be in the game to shift it, and we are inheriting the largest wealth transfer probably in our history. We may want to play it safe because it hasn’t been a safe dynamic for us our whole lives. It doesn’t mean that we can rest on that. We’ve got to push into it, learn a different language, and we’ve got to get comfortable with it. We have to set the agenda with our money and put our money where our mouth is and bring our values.

AMANDA STEINBERG: We have to create a collective vision of what we want the world to look like, and then we have to build it. We cannot wait for anyone else to do it.

JENNIFER BROWN: Absolutely. Thank you so much. Please buy Amanda’s book, everybody. Read it, take notes, highlight every page. Put your money in play. Thank you so much, Amanda, for joining me.

AMANDA STEINBERG: Absolute pleasure.



Get your copy of Amanda’s new book: Worth It: Your Life, Your Money, Your Terms