Jennifer Risher is the author of “We Need to Talk: A Memoir About Wealth” which tells her story and explores the impact of wealth on identity, relationships, and sense of place in the world. Jennifer was born in Seattle, Washington, grew up in Oregon, and graduated from Connecticut College. She joined Microsoft in 1991 where she worked as a recruiter and then as a product manager.

She and her husband, David, have two daughters and live in San Francisco, where David is CEO of Worldreader, a nonprofit he cofounded with a mission to create a world where everyone is a reader. In response to COVID, Jennifer and David launched the #HalfMyDAF challenge, which inspired over $8.6 million in charitable giving in 2020 and aims to help move over $20 million in 2021.

From YouTube channels to get-rich playbooks, whole industries are devoted to the subject of building wealth. But few books present a clear and honest view of what it’s like to have a lot of money. Today we welcome author Jennifer Risher onto the show to share her insights on living with wealth. Early in the episode, we explore how Jennifer and her husband ‘hit the lottery twice’ by being given stock options for both Microsoft and Amazon before they went public. Jennifer then shares details about the key premise of her book: people with wealth never talk about their money. Informed by her experience of having sudden wealth, we discuss why gaining wealth doesn’t significantly change people despite it leading to feelings of isolation. After talking about how wealthy people rarely feel that they have enough, we unpack the many benefits that come from talking about your wealth. As Jennifer explains, using examples from her life, communicating your feelings about money is a solution to many relationship issues that arise from having wealth. Linked to this, we dive into how you can raise balanced children whose outlooks aren’t spoiled by affluence. Later, we touch on the role of giving, Jennifer's top advice for newly wealthy people, and how Jennifer views work now that it’s optional for her. We wrap up our conversation by hearing about how the wealthy make a positive impact on society. In this episode, we dispel many myths about being rich. Tune in for more on why we need to be talking about wealth. 

Key Points From This Episode:

• Details about author Jennifer Risher, today’s guest. [0:00:17]

• Jennifer shares why she wrote her book and the problems that it addresses. [0:02:43]

• Exploring the question: how much does wealth change you? [0:06:55]

• What wealth has given to Jennifer and what it hasn’t. [0:09:10]

• Jennifer describes the feelings that came with suddenly becoming wealthy. [0:10:14]

• The process informing Jennifer’s decision that she had ‘enough.’ [0:13:41]

• Hear Jennifer’s advice for couples who have different definitions of ‘enough.’ [0:16:49]

• How few wealthy people don’t feel that they have sufficient wealth. [0:19:03]

• The important role that financial advisors play aligning wealth with people’s values. [0:20:13]

• How Jennifer’s book is opening up the conversation on wealth. [0:23:09]

• Challenges around raising children in a state of affluence. [0:25:36]

• Why modelling virtuous behaviour is key in raising balanced children. [0:28:40]

• What Jennifer learned from speaking to other wealthy couples. [0:30:23]

• How having wealth can impact your relationships. [0:34:06]

• Overcoming the taboo of talking about money. [0:38:52]

• Ways to view work when working is optional for you. [0:42:28]

• Jennifer unpacks her biggest lessons on giving. [0:44:00]

• Jennifer shares her advice for newly wealthy people. [0:50:35]

• What the wealthy can do to improve society. [0:51:59]

• Hear how Jennifer defines success for herself. [0:53:34]

Read The Transcript:

I think many of our listeners have actually checked out the book ahead of this conversation. So, off the top, Jen, can you tell us why you wrote this book?

I certainly can. I'm very lucky. When I was 25, I took a job at Microsoft, and I met my husband, David. And I got stock options that ended up being worth hundreds of 1000s of dollars. Six years later, when Dave and I were married and expecting our first child, he took a job at an unknown startup that was selling books on the internet, called amazon.com. And we were in our early 30s, the company went public, and we really had more money than we could wrap our heads around. And I want to say up front, that money makes life easier, but wealth surprised me. Having a lot of money doesn't look or feel like what Hollywood sells us. I felt the impact as a parent, as a sister, as a friend, as a daughter. It was painful to feel my parents disapproved of what I had. Eight out of 10 people with wealth grew up middle class or poor, and we're not talking about the emotional challenges.

So it might be hard to think of wealth as a challenge that needs to be overcome, especially now when there's so much need. I mean, COVID is shining a light on racial and economic inequality. I should pay more taxes, minimum wage needs to be higher, we need a stronger social safety net in the US. Reparations need to be made. There are so many policy changes that need to happen. But I think change also needs to happen at a personal level. I want to help us move money out of the taboo category, out of the shame category, and get us talking to each other, because normally, if I have a challenge, I talk to my friends. If I want to figure out should our 16 year old have a curfew, I talk to everyone I know. I get their ideas, I get their advice, I hear about their experiences. And just talking is helpful because it lets me know my challenge is normal and that it's valid and that it's shared.

But the same doesn't happen with money. And I couldn't talk to friends about having a lot of it. So I thought, okay, I'll turn to books. But there are no books. So, to answer your question, why I wrote this book, first, my story is one I'd want to know about if it hadn't happened to me. But I also wrote this book for the millions of Americans like me who have more money than they had growing up, or they have more money than many in their extended family, or more money than many of their friends. I'm sharing my story as a way to help other people understand their own. And my goal is not to show people how to do rich right, I don't have an answer for that. My story's not prescriptive. I'm offering up a story that hasn't been told, that explores things like how hard it can be to navigate a vacation with another family that doesn't share your resources. Or how upsetting it is when you feel a friend's jealousy and you can't share what's really going on in your life.

I'm telling my story to help other people, and I also am telling my story to get us talking, because the more I talk about money, the more I realize it's not money that we don't talk about, it's the emotions behind the money that we avoid. And these emotions are universal. It doesn't really matter how much is in your bank account. If you have parents, if you have a sibling, if you have a partner, if you have friends, you know that money is a hard topic to discuss. We're afraid. We're afraid of hurting someone's feelings, we're afraid we won't measure up, we're afraid of rejection, we're afraid we won't sound knowledgeable. So we don't talk about it. And yet, we all have some degree of money shame, we all have a money story that starts in our childhood. So my goal really is to help us have conversations that need to be had.

One of the things that I appreciated about the book is it's not just your story, you also discuss a lot of the things that you went through with other wealthy families, and then give their insight and then bits and pieces of their stories. That makes the whole experience of reading the book that much more powerful. You mentioned that money makes life easier. Is there anything that wealth has provided you and your husband, David, looking back that your younger not wealthy self would not have expected wealth to provide?

There's so much my unwealthy self, in high school, I think maybe everyone's done this, what would I do if I had a million dollars? You ask yourself that question, and then you start to fantasize. And of course, at the time, I thought I'd have a cute boyfriend and a fancy car. But really, I thought all that money would change everything, that my life would be perfect. I think we often set ourselves up this way thinking if only, then my life would be perfect. And we do it a lot around money. If only I could get that big promotion, we do it around other things too, if only I could lose 20 pounds, if only I met the right, then my life would be perfect.

I had an if only happen, and I'm still me. I still have insecurities, my feelings still get hurt. I make mistakes. And I'm not in a fantasy land. Our view of wealth is so narrow and incomplete. We see the Kardashians and the Real Housewives and the men of Wolf of Wall Street, and we know about people like Jeffrey Epstein or the parents who illegally tried to get their unqualified kids into top schools. We see the highly visible wealth, the stereotypes. But remember, eight out of 10 people with well grew up middle class or poor, and they are you. And they're hidden in plain sight so much more ordinary and so much more diverse than what we see.

And so, that for me was a surprise. We have these fairy tales in our heads that make the reality kind of more just so different than what we expect. And I think one of the things, did you ask what wealth has given me or what it hasn't? I mean, I think there's both. I would never have guessed that I would be giving money away. I mean, just like we all have a money story that starts in our childhood, and in our childhood, we either learn about giving or we don't. And when I was growing up, my mom and I took canned peaches to food drives and clothes to the goodwill, but my dad generally had the sense that charity is for chumps. When we passed someone on the street, the idea that he was asking for money was sort of like, well, they're trying to take advantage of us. So I didn't grow up with the idea of giving. And so, that's been a journey in and of itself, and that's been a privilege and a surprise that I wouldn't have expected.

I guess I expected there to be a lot of freedom, and there is. I mean, there's so much opportunity, money does mean make life easier. But it's not as though that freedom just sits there and you just can walk through this, you still have to make things happen, you still have to make decisions, you still have to take risks. It's not the fantasy that I had imagined.

So when you were amassing wealth while at Microsoft, you can see the company that was public. So, I suspect you had more awareness over how things might play out. But when David joined Amazon and then they went public, I suspect that was a little bit different. Can you talk about how that might have been different or some of your big concerns when that happened?

Yeah, with Microsoft, this was 30 years ago, and things were, no one knew what a stock option was, even when I started at Microsoft. Suddenly, we had this numbers on paper that was just kind of getting bigger and bigger as the stock was going up. So we kind of been watching that. But it seemed so far out in the future. And then when David, I mean, it really was just this startup this guy had started from his garage selling books. My husband loves books, he loves technology, he thought, this is a great opportunity to make a difference with books and technology. And then all of a sudden, the company goes public. That was really shocking. Of course it was amazing, but I think my real feeling was I got to keep this hidden.

People think that the wealthy worry about other people liking them just for their money, but I wasn't worried about being liked for what I had. I was worried about being hated for it. And I just didn't want anyone to know.

Do you think other families that went through a similar situation had a similar experience to you?

Even at the time, I mean, it was nice that we had friends who were at Microsoft who were kind of going through the same thing. But we never really spoke directly about money and its impact and the impact within our families with our parents and kind of worries around children. So there wasn't enough conversations about this. So, it felt very isolating, the distance it can create within relationships. Again, it just felt quite isolating.

On the outside, there's all sorts of crazy stuff happening where back at Microsoft, people were starting this cash in their options and buy houses. You'd see people buying houses or cars, and then we'd sort of laugh the Honda Accord that someone just bought was now a $300,000 car because the stock had gone up so much. We had a friend who bought a 900 square foot bungalow, and I think that's the most expensive house he's ever owned.

It's crazy to think back like 30 years later, what you two were at the beginning of, and what's happened in the past 30 years. Can you talk about the social dynamic between Microsoft and Amazon, friends who may have sold early and others and may have held on longer? Was there open conversation about that?

Not really. There is definitely that. And then we had a small group of us, we did well, we were very lucky. The group of people that I know, still know from Microsoft has done quite well. It was never like people were going bankrupt or broke or whatever because they spent, overspent. I don't know any people like that. At Microsoft, it really was frowned upon to be too, I mean, Seattle is a pretty kind of low key place. And so, there wasn't a lot of overspending and flashy spending, that was just kind of not the way the culture was. So, not many people kind of blew all their money, similar at Amazon. People were working really hard too, so they didn't have time to really spend a lot of money, and that's true.

You mentioned in a book that in the early 2000s, when the Amazon share price was dropping along with everything else, also pulling your net worth down because as you mentioned, a lot of that was in Amazon, but you mentioned in the book that you weren't too worried because you felt that you had enough. Now enough is a hard concept because humans always want more. What convinced you at that time that you had enough?

Enough is tough. Actually, I don't think there is ever enough, just as there's no perfect. These things are kind of illusory. And it's very interesting because it's so relative. Back when I was talking about the high school kid that I was, dreaming of a million dollars, once you have a million dollars then there's $2 million. And once you have $2 million, then there's 10. You can find yourself, there's never enough and there's always more, and there's always less. I think it takes realizing that you're not going to find enough outside of yourself. You can be spending your whole life chasing after enough, and I realized that I didn't want to do that, that was not where happiness was going to be found.

So I really made a conscious decision, and I really looked around, like yeah, we have enough, more than enough, and it was a conscious choice and a mindset that I had. And that doesn't mean to say that it doesn't come back and there's not moments where I feel a little panicked or a little like, oh, do we have enough. But then I just remind myself again, I think it's important for people to do that, to really look at what they value, what their goals are, what they have in their life, and look at the positive, and feel the abundance rather than always chasing more.

To tie this back to the previous question, did having enough have any relationship with whether you continued to hold or sell shares in Amazon?

Now, I think our focus is so changed. When all that happened, we had young kids, we were a young family. Now our kids are out of college and our focus, my focus, I mean, both of us, we want to do good in the world, and we have this added tool that we can use. So now it's like, yeah, I'm not looking to how much more we can have, I'm looking to how we can kind of make a difference and have an impact and use our money to help others. My husband started a nonprofit 10 years ago and works full time on helping people have access to books. He's shared that love of books and technology and created a nonprofit called World Reader, getting digital books into the hands of kids throughout the developing world.

Now with COVID, there's an education crisis here in the United States, and he's partnering with people here and bringing World Reader here to help kids continue reading and continue learning. So, I think that feeling of enough is definitely there because now it's like, how can we give to others and focus on returning some of the money that we have to the world.

So you and David met before you had all this wealth, and you mentioned two great quotes, enough is tough, and feel the abundance. So even the fact you met before you had the wealth, any advice for couples who may have different definitions of enough even before they think they have enough? How do they have this conversation, be prepared for what economically might happen?

I feel fortunate, even though Dave and I have slightly different views of money and ways of dealing with it, but we share common values and common goals. I think that's what made it easy for us to navigate this because we pretty much agree on kind of where we want to be and how we want to walk through the world and live our lives. It's hard in any relationship, it's a negotiation. And so, our people, when one person feels that they have enough and the other person doesn't, I mean, that's a tricky negotiation in a marriage, in any aspect of a marriage. Do you want to have another child or do you want to have children? Do you want to go on vacation or do you not want to go on vacation? Do we need a second home? All those kinds of conversations are about values and what you care about and how you want to live your life.

And I think money is a real, it can be, I mean, it is. Technically research shows us that it's a source of stress in relationships. I think the key is being transparent talking about it, being open about it. People don't talk enough about money, it's such a taboo subject, but it doesn't have to be. And we need to move it out of the closet and give it light and talk about it like we talk about every other thing in our lives. I think couples need to talk and work through kind of when one feels, and I'm thinking about a couple who she feels that they have enough, and he still wants more, he's still seeking so he's still working nonstop. But it's not really for him about the money, I think he doesn't feel like he's been successful enough, or he's still seeking the success. Is that going to tear a couple of party? It could. Does she kind of support him in the work he's doing? It's a constant negotiation. I've been married for 25 years, and it's a negotiation.

What have you found in talking to other wealthy families regarding that concept of enough? Do people with wealth generally feel like they have enough, or do you think that there's a lot of wealthy families who are still hoping for more?

I'd say unfortunately, people don't feel that abundance. And I think it's a problem. I mean, it's a problem for them how they feel day to day. The research shows, John Rockefeller always wanted a little bit more, he never had enough, and he was the wealthiest man in modern history. There's a study out of the Center of Wealth and Philanthropy at Boston College that was sponsored by the Gates Foundation, this was in 2008, that kind of talked to 165 wealthy families. The medium income was like $78 million. And did they have enough? No, they wanted 25% more then they'd have enough.

And I think we do this to ourselves, I think it's a travesty really that we do this to ourselves. There's always gonna be someone with more and there's always going to be more out there. But if you want to spend your life chasing that, I don't know if you're making a good choice.

There's a story in your book where you take your concerns about raising your kids in a wealthy household to your financial advisor. And I believe he came back with some estate planning advice. What do you think a financial adviser can do to help you with your conversation about wealth with your kids?

First of all, just acknowledging that this thing is supposed to be only positive has a lot of challenges to it, and that the questions and the issues and the complexities that come up are real. Not only acknowledging that, but I think one of the things that we wanted to know is what are our peers doing? What are other people like us doing? And because we're not talking to each other, and this has surprised me too, I thought, oh, when you have wealth, you're suddenly in this big, sparkly private club, and you're sharing financial secrets. No, you're in this very strange silent space where you don't know what anyone else is doing and you can't talk about money because it's not okay, and it's certainly not okay to talk about having a lot of it.

And research shows this too, that people with wealth really don't talk about it. But we should be. And I think advisors can help us do that. And advisors telling us what our peers are doing, or even better than that, connecting us with other people like ourselves. Maybe even giving us a script or several questions to discuss together.

In my book, I have questions at the end of every chapter. Give couples my book, have them read it, and come together and talk about the issues that I bring up. It's such a relief to hear other people's stories, it normalizes what you're going through, it validates. But it also helps you learn because with other things, you ask other people, you talk about things, and with wealth, you don't. So advisor can connect people who have similar situations going on, connect them.

The other piece is philanthropy. I mean, people also don't know what to do around philanthropy a lot of times, and it becomes a source of stress. A financial advisor has so much ability to help people through that whole process of finding out what do you value, where are your passions, where are your interests. And then helping people find nonprofits and organizations that are working in the area of their interest, introducing them to those nonprofits. But holding their hand and helping them start to actually give because it takes time. Your net worth and how much you give her not connected, you have to start with $1,000 gift or a $5,000 gift. And then you're a financial advisor and you come back and say, let's do a little more, let's explore this other nonprofit and help them build relationships with nonprofits. There's so much I think an advisor could do to help people who really don't know what they're doing in the space of learning about other people like themselves, and also working with philanthropists or working with nonprofits.

Has the process of writing this book or maybe now having the book opened more doors for you to talk with other wealthy families? Is this an easy foot in the door to have these conversations now that you've got this piece of public work out there?

Absolutely. I'm finally out. It took me 14 years to write this book. And towards the end of that process is when I thought, I need to interview some other people and include their voices to add different perspectives to my story. And even then, I was nervous, I was scared to reach out to people and ask them to talk to me about having a lot of money. I really had to fight through my fear. But when I sent that email to a couple of acquaintances just talking about my book and asking if they'd talk to me, the response was amazing. People said, I think about these things all the time, but I never talk about them.

So just opening that door, the conversations that we had, we got together, and we talked about our kids, and we talked about our parents. And we realized, oh, we're not alone, we have so much in common. And we have so much to learn from each other. So, now that I'm out talking, I've gotten so many amazing notes from people thanking me for writing the book, saying that my story resonates, that it's so helpful to hear, that all my feelings, I'm not alone, that sort of sense. And that's my goal now is really to help us start conversations because we can connect and we can learn from each other.

And then I think it may sound far reaching, but I think we can also fight income inequality through talking and making this really shining light on the reality of wealth, because our silence has a lot of power. Our silence keeps the status quo in place. It keeps us from examining our relationship with money. It allows us to stay in our bubble unaware. When there's a large and influential segment of the population that isn't talking to each other and feels estranged, we're probably not at our most empathetic or generous, and we're probably not holding ourselves accountable or inspired to make change. I think it's important for us to talk as people, as individuals to learn from each other. But also, I think there's more that can happen here. This is not a society I want to be living in. There's too much disparity, and I think we can help bring that together by conversations, that just aren't happening right now.

One of the other things that I think comes up with wealthy families, and we've talked about it a little bit, but I want to get a little bit more specific, is just concerns around raising children and how the children are going to be raised. What are some of the biggest concerns that you and David had raising your kids in affluence and what have you done to deal with those concerns?

This is the question I get all the time, how do you raise kids that aren't spoiled. And I think now, there is this huge myth out there. It's part of the whole myth of what wealth is, it's the spoiled rich kid. And this spoiled rich kid is so big in our psyche. I don't think it exists. I think we are so fearful of this. No one wants to raise a spoiled kid, and then you add wealth to that, and you're like, oh my gosh, I'm going to raise a spoiled rich kid. I lived with this myth for decades, I was worried about spoiling our kids. I think if you live your values, your kids are watching you. It's not sitting your kids down and telling them your values. It's day to day, week to week, year to year. Your kids are watching how you interact with other people, how you think about things, how you move through life.

Going to the grocery store, when you drive up to the grocery store and someone steals your parking spot, what do you do? Do you feel entitled to that, are you yelling, are you gracious? However you react, your kids are watching. You walk into the grocery store and they see you making choices and trade offs. In fact, that's a teachable moment. How are you thinking about the price of things and the quality of things? They're watching those decisions you're making. They watch as you go to the meat counter and you interact with the person there. Are you respectful? Are you generous with them? How do you interact with other people? It's a lot about attitude and gratitude. So, everything in your day, you're kind of showing your kids what you value. Sitting around the dinner table, what do you talk about? What are you proud of about your day? What are you worried about?

So, I really believe that if you are living the way you want your kids to be able to live, that's how you kind of raise kids that aren't spoiled. I think we need to get rid of this whole myth of a spoiled rich kid. Money is not what spoiled kids, it's parents. And kids can get spoiled No matter how much or how little you have. It's the way you interact with the world and with your kids.

Wow, that's really interesting. There's not being spoiled, and then there's, you've talked about a few things like solving wealth inequality or at least improving it, and philanthropy. On the maybe opposite spectrum of not spoiled, and I know you said earlier that you're not trying to tell people how to do rich right, but do you think there are things that you can be teaching kids specifically about using wealth in a positive way as opposed to not just, not being spoiled, but how do we take this wealth and make the world better? Are there ways that wealthy parents can talk to their children about those issues?

Yeah, again, I think this gets back to what I said earlier, it's really modeling. Your kids are watching you. So, they've watched my husband spend the last decade focused on helping kids in the developing world get access to books. All his time, every day working on World Reader, he's the co-founder, he's now the CEO. He works nonstop on this. They're seeing that. They've grown up with mom's book, I've been writing my book for a long time. They've seen me work in the school. They like when I come in, or they used to at least when they were little, come in and help in their classroom and be part of the school. They see what we do, and I think that is the most powerful lesson. I said before, it's about attitude and gratitude. Yeah, we still, we get to go out to eat, we've done a lot of traveling.

But when we do those things, my husband and I are so grateful, and they hear us talking about how lucky we are and how fortunate we are to be able to travel. And traveling too has been a source of learning for them, because we spent time in China and we stayed in a dormitory for two weeks and we taught in a school. So they were part of teaching in the kindergarten in China. And when we went to visit Vietnam, we had purchased a house for a family and we went to that house and we had lunch with the family, and we helped finish painting the trim. They are very privileged and very fortunate, but they also have seen different ways of living. We lived abroad for many years, so they know that there's a bigger world out there, and I think that's important.

I'm really curious about these conversations you have with other people. I'm curious if these conversations changed how you and David made different decisions or did it help give you confidence in your own decisions? Did you go into these conversations trying to learn things, or was it more about just experiencing other people in their situations which helped you make your own decisions? Were you going out trying to get an answer to a certain specific question you may have had, or is more just to find a place to have a sounding board to think through different issues that you and David may have been wrestling with?

It wasn't really until our oldest daughter was going away to college that we really talked about money with anybody else, and really had serious, honest, open conversations. I was writing the book and I was really feeling overwhelmed. We felt like we had to really talk in more depth to our kids, and I was really worried, again, this spoiled, rich kid, entitled kid is still in my head. I also feel like it's a lot of pressure for a kid to know that they have a lot of money. So I just didn't know how to talk about, it just felt overwhelming, and I had no model for it. My husband and I just sent a note to a couple other couples and said, will you sit down with us and talk to us about how you talk to your kids.

And here again, I mean, there's definitely a pent up energy around wanting to talk about these things because the emails came back so fast. Yes, we'd love to talk to you, and then when we sat down to dinner, we spent two hours over dinner talking about how they had kind of handled money with their own kids. And it was so helpful, like one couple talked a lot about, they thought a lot about housing, they had three kids and they were trying to tailor gifts to each of their children around housing. And then they kind of realized that no, they wanted to make it equal to all the children. And then they shared that they had given this amount of money to each of their kids, and one of them had bought a big house, and the other had bought a smaller house and put some money in the bank. And then the third hadn't yet purchased the house.

Just hearing about other people's thinking and experiences is so helpful. It kind of made it less overwhelming. Another couple told us about how they had their kids meet with their financial advisor alone and talk about that they had a trust and they had written a formal letter to each of their children, explaining that the money is theirs, put them to use in any way they wanted. It felt very formal. They also talked about how they had put money aside for their kids' college. And I like that concept. We picked pieces that worked for us. It really helped kind of normalize and validate our own feelings around this. And then when we talked to our kids, it just felt like any other conversation. It sort of put money in its place. And so, we told our kids that we had put this money aside for their college, and that's how we were paying for college, and then we told them that we'd also put some money aside for them in a trust. It was just a normal conversation, and it was just such a relief to have that conversation with other couples.

But those conversations aren't happening as much as they should. And I think, again, back to the financial advisor, if a financial advisor can help set that up for other clients that they work with, and it's funny, I think back to 30 years ago, I would have been horrified to think of doing that. But if I had done that, it would have been such a good thing for me to help normalize the money instead of just hiding it. So, if our financial advisor 20 years ago had said, here, read this book, or here's some questions, I want to introduce you to this other couple, you guys go out for dinner and have at it, sort of thing. That would have been so helpful. I wish that had happened, and I think that that should happen for other people.

You mentioned when you were talking about why you wrote the book the potential for wealth to affect relationships. Can you describe some of the ways that wealth has affected relationships in your life?

Yeah. I'll share some stories. A friend of mine a year, it's a good friend of mine, and she doesn't have the same resources that I do. But a year after the fact, she told me, "We almost didn't invite your family to join ours to see [inaudible 00:34:35]." And I said, "Really, why?" And said, "Yeah, I agonized for weeks. I was worried that if I asked you to join us, you'd only want to sit in the front row seats and our family can't afford that." And I felt terrible. I hated to think of her worrying about the finances. Our friendship meant more to me than front row seats, didn't she know that? But I was so glad she trusted me enough to talk about money.

Having that conversation really brought us closer and made me feel closer to her. It also opened my eyes to how out of touch I could be, and how unaware and how in my own bubble, which is another reason that conversations are so important. I'll share another story, this is a again, a friend who is middle class, she told me how she and her husband had driven the same car for many, many years. And she said, "When that thing finally broke down, I bought an Audi Q5." She'd always wanted that car and she loved the car, and she was excited about the car. But then when she was thinking about visiting her sister and driving up in the car, she said, "I was worried about being judged." So in her mind, she heard her sister saying, "Oh, aren't we fancy." And then in her mind, she started to justify the car saying, it was used, it wasn't that expensive.

So even before she saw her sister, she was making assumptions and telling herself stories. What if she'd actually talked to her sister. And I think we do this all the time to ourselves. We tell ourselves stories around money, and we have ideas that aren't necessarily true. When you don't talk about something, it tends to loom large, and take on a life of its own. So I'll share one more story, this is between me and my brother, and I have a brother who's two years younger than me. And when he graduated from college, he went into the Peace Corps, and then he got a master's in Spanish and became a high school Spanish teacher. And this is many years ago, he wanted to buy a house. And my husband and I offered him $20,000 for the down payment. But he refused our gift. He said he wanted to live within his own means.

And this refusal hurt my feelings. I at the time felt like he was looking down at our money, and my feelings were hurt, but I didn't say anything. And then a few years later, when he was getting married, Dave and I sent a check, and this time he accepted this as a wedding gift. And then when his first child was born, we again sent money, and he and his wife thanked us. And we began to send money every year over the course of many years, he stopped acknowledging the gifts. So I'd write a check in December and hear silence. It was like the money was sort of disappearing into a void. And I began to feel resentful, and I felt like I was being taken for granted. But I didn't say anything again.

And I'm not proud to admit this, but a couple years ago, just didn't send a check. In January, when we were communicating over email, at the end of his note, he said, "Wondering if a certain year end check is just late in the mail. Is it?" And I read that and I was shocked and angry. And of course, I knew we needed to talk. But again, it was not comfortable, and I really had to sit down and figure out how I felt, and when we have to talk, and I got on the phone. And when we got on the phone, I said, "My feelings are really hurt that you haven't acknowledged our gifts." And he apologized right away. He said he hadn't realized that he thought that it was more comfortable for me if he didn't make a big deal of the money, which I completely understood because that's how we grew up.

And then, once we were talking and connected and two people who love and trust each other, that's when money was put in its place as a tool, not as something bigger than us, but as something that we could then talk about easily. I mean, really, once we had that connection, he said, I don't need this money, but I really appreciate it. And I said, I don't care what you're doing with it, but what are you doing with it? I wanted to know, I wanted to be part of his life.

Talking about it sounds like, in a lot of those cases, was a solution. There's a story in your book where you're you're going on a trip with another family, and you wanted to offer to pay for tickets, but you were worried about bringing it up. And you tried to and they rejected. Do you think in a case like that having an open conversation is still the solution?

I think in the most part, yes. I think as transparent as we can be, the better. I want to say, again, it's not easy because this is not a muscle that we've built. We don't know how to talk about money, and it's such a taboo, and it's so considered impolite that we're fighting against a lot of social norms telling us not to talk. But I think we need to try and we need to push through that because as I've found on the other side of that conversation is usually a sense of relief, a sense of connection. And then a chance to really grow and learn. It's kind of one of the more intimate conversations that you can have where you can really feel connected to someone else.

Of course, there's going to be times when it's not going to go well, but that's the case always. You can't always find that perfect connection. I would encourage everyone to try, start by figuring out what you're feeling, what are you really feeling about the situation. Let's say a friend is always asking you to go out to a restaurant that you really can't afford. Or let's say your daughter buys a handbag that's not within her budget, or doesn't fit your values, or your in laws are giving to your spouse's siblings, but they don't give any money to you. Or you go out with a couple and they're constantly talking about all the stuff they're buying, and it's annoying.

So all these situations are things that we avoid, but I want to encourage us to not let those hang over our heads and avoid them, but to actually have a conversation around them. I think it starts with figuring out what you're feeling because money is emotional and it brings up a lot of feelings, whether it's anxiety, or intimidation, or stress, or jealousy, or resentment, or joy, or pride. Just so much there. In the case of a friend always wanting to go to an expensive restaurant that you can't afford, okay, what do you feel there? What's coming up for you? Is it resentment? No, actually, it's shame. You're ashamed that you can't afford that restaurant. You should be able to, you have a good job. So you're feeling ashamed. So figure that out.

And then two, find a time that's mutually agreeable and emotionally neutral to have a conversation with that friend. And when you have that conversation, three, is acknowledge that it's going to be uncomfortable. Give each other permission to fumble around. We don't know what we're doing so it's going to get messy. So, by acknowledging that this is an uncomfortable conversation to have, I think you can create sort of a safe space where you can have this conversation.

And then four, really listen. You get to talk for five minutes uninterrupted, share what you're feeling, and then your friend gets to talk for five minutes uninterrupted. And maybe your friend says, oh my gosh, I had no idea, dinner's on me, let's go, I'll pay. Or maybe your friend says, oh, I don't care where we eat, let's go somewhere less expensive, it doesn't matter. I want to spend time with you. Or maybe your friend says, wow, thank you so much for saying something, I'm in a lot of debt. I shouldn't be going to those restaurants either. So, you really don't know until you have that conversation. And then at the end, I bet you'll feel more connected and you can show your gratitude. Thank your friend for having that conversation with you.

I have a question for you, Jen, about working. So in your research, as well as your own and David's experience, what have you learned about the role of working when work is truly optional in your life?

There's another fantasy like we always think. Oh, if I didn't have to work, I'd sit on the beach or I'd go out with friends, it would be just so wonderful. Yeah, for a couple weeks, it really is very nice, and I think the fantasy of not having to work, it's big in our minds too. But work gives us a lot and it places us in society. It gives us a reason to get up in the morning, it gives structure to our day, it gives us camaraderie with our colleagues, it gives us goals to achieve, a sense of purpose and meaning. It's much more than just a paycheck. I felt that right away when I left Microsoft. My identity was really wrapped up in work, and I realized how much I was getting from work, and then not having work.

It can be very challenging, especially when in the US, we kind of define each other through our work. Often the second question someone asked you is what do you do? What you do is your work. And when you don't have that, it can be more challenging than we realize, to find that sense of purpose. Because I think, where does happiness come from? It does come from feeling a sense of purpose, making a difference, having meaning in your life. It comes from being generous with other people. Ultimately, from the connections you have in your life, and your work connections are part of that.

We've touched on philanthropy a couple of times. You mentioned in the book that your understanding of giving evolved over time after you had come into wealth. It wasn't like you immediately understood. Can you talk about what some of your biggest learnings are as it relates to giving?

Yeah. Like I mentioned before, I didn't grow up thinking about giving money away. It didn't feel like there was any extra to give. It wasn't really until I got to Microsoft and I was surrounded by peers who were making charitable donations that I gave a small percentage of my paycheck to United Way, I gave $1,000 to Planned Parenthood. At first, it was just starting to give, and then it was giving to places that were giving to me. So we started to give to NPR, and I was part of a mother's group when our first child was born, I gave to that organization.

And then sort of the next step was when our kids were in an independent school, and that's a whole learning in of itself, it's like entering a foreign world because suddenly I was learning a whole new language around giving, I was learning about development and fundraising and [inaudible 00:45:10] and stewardship and capital campaigns and endowments, and all these things that I knew nothing about. And at the same time, our financial advisor, we had this Amazon stock, and there was a point where he suggested we put some money in a donor advised fund. So this is a charitable vehicle where you get your tax break up front, you put your money in, then you can give over time.

We put a bunch of money into the donor advised fund, and I learned that you know, letting go of the money isn't the hardest part. Figuring out where to give felt really overwhelming. And again, this is where I think a financial advisor can really be helpful to people, helping them figure out kind of where they want to give in their passions and introducing them to different organizations. And for me at that time, I felt like I had to have a philanthropic strategy. I had to have done all the research, I had to do giving perfectly, I had to get it all right. And my fear of getting it wrong kept me stuck and not doing anything. And there were a lot of excuses, we had young kids and we didn't know what we were doing.

But it took time to figure this out. Fast forward now, so last year during COVID, my husband and I launched this campaign, and it really came out of just our hearts going out to nonprofits. We were experiencing it from the nonprofit side because David with World Reader, he had foundations that had kind of promised to give him money and they were kind of backing away because everything was so uncertain. And this was when the stock market was dropping. It felt like all the funding was just drying up and our hearts were going out to nonprofits, and we wanted to help do more. And I was already kind of doubling down on places that I was already giving to, and kind of accelerating gifts that I kind of given out three years, I was kind of giving immediately.

But we wanted to do more to help nonprofits, because the need was greater than ever. So we thought we just need to start giving to nonprofits. At the same time, I've learned a lot about donor advised funds. So in the donor advised funds, there's a ton of money stuck there. People have put that money into donor advised funds, but it's not moving through. And there's $121 billion stuck in donor advised funds. And actually, that number is now bigger than ever. I think it's 140 if not greater. Money that's philanthropic charitable dollars not moving out. And so, that's frustrating.

And so we thought, well, how are we going to make our money go further and how are we going to help kind of inspire people to start giving. So what we did is we offered up a million dollars in the form of matching grants for anyone who moved half of the money out of their donor advised funds to nonprofits. So we started the #HalfMyDAF campaign, and it was very successful. So we got a lot of press early on, and our million dollars ended up moving a total of 8.6 million from donor advised funds into nonprofits in just five months. So we launched it in May. And technically, that's a huge success in terms of the numbers, but it also felt very successful in terms of the community that it created. Donors were so thankful, they were like, this is the nudge I needed. I'm inspired to give. I'm sitting around the dinner table with my adult kids, we're talking about our values and where we want to give. Having conversations that they otherwise wouldn't have been having.

And then also the connection between the nonprofit and the donor, it was such a great opportunity for a nonprofit to reach out to a donor and tell their story, ask for donation, and then tell them about the opportunity to get a matching grant from #HalfMyDAF. So it was building relationships between donors and nonprofits in a way that I think is so important. So, we were thrilled by that #HalfMyDAF challenge and the success there.

It's a very cool story.

This was sort of a one off thing that we thought we would do, and it was, we started to get people saying, when you do this next year, can I participate next year? And so now we have launched #HalfMyDAF 2021. Last year, we put up a million dollars and we actually had people join us in the matching pool side. So we ended up being able to give 1.4 million. This year we have over three million to giveaway. The people who matched us last year came in with more money, they had a good experience, they felt like it was leveraged and it was doing the right thing. So people who had given 100,000 last year gave us a half a million.

And you asked earlier about our kids, how they learn, and I have always said that they've kind of experienced it. And I think I can say with great pride that we got the best Christmas gift ever, they came to us and said they wanted to be part of HalfMyDAF. They had talked to each other and then talked to our financial advisor, and they also have contributed money to HalfMyDAF. And they wanted their money to go to specific causes. So this time, instead of just matching any gift, we'll match any gift, but then we also have specific money for racial justice, environment and climate, for education in underserved communities, and for reproductive health. So our goal, again, is to inspire giving, and people can give wherever they want. But if you're going to give to any of those areas of interest, there's more money there.

Wow, such a great idea. There's a whole new generation of newly wealthy people emerging all over the place today. What is the one thing that you would share with them that you wish you had known 25 years ago?

I would tell them, you're not alone in how strange this is. And talk about it, don't try and hide it because I think there's this feeling of, for me, it was sort of like, if I talk about this, in the name of connection, I wasn't kind of sharing what was really going on in my life. But that doesn't really make you feel connected. So if you're walking around keeping things hidden, keeping a part of what's going on in your life hidden, it's exhausting, and it's not very fulfilling, and you don't feel that connection. So, it can be very uncomfortable, and it takes time to kind of get used to a new, wealth can be challenging. I know it sounds crazy, but I think talking about it, getting conversations going as soon as you can, is what people need to do.

And I think here again, I call on the financial advisor to help people through these emotional challenges that come up. And it's often within immediate family and between friends. And because what we care about most, what makes us happiest as human beings is our connections with other people, that's something to really think about and to focus on and keep those connections open and transparent as much as we can.

You mentioned earlier in terms of what the wealthy can do to help improve society. One of the things you talked about was just talking about and having these conversations. Is there anything else that you think that the wealthy as a group can be doing to move towards solving some of the issues that you've talked about?

I'm so glad we have Biden-Harris in the White House. I think we can vote in people who are going to, I mean, there's so many people going without housing, without health care, without food. There's an education crisis going on. When there's people hurting in our society, we're all hurting. We're interconnected, we're part of a bigger whole. I would say we need to kind of advocate for paying more taxes, we need to advocate for a society where there's a social safety net for everyone. Advocacy, but also, if we're not talking to each other, if we're not realizing our own privilege and coming up with ideas, the conversation David and I had around COVID in the backyard, we kind of came up with this idea of HalfMyDAF, there's so much more we can do in the philanthropic space as well as just in our personal lives. If we're having conversations, I think that's a positive thing.

Right now, there's just too much silence. So the more transparent we can be, the more we can put money in its place as a tool that we can use in society to help us all, I think the better. We all win when our society is healthier as a whole.

So interesting, we've learned so much about you. I still have to ask you a final question, which is how do you define success in your life?

I think it is being true to who you are, being as authentic and transparent as you possibly can be. So success is living your true self, living what you value, and having the courage to take risks. I think this book is, no one has written this book, but so many people could have. And I'm realizing that because people are telling me how much they relate to it and how important it is. So, I feel proud to be shining a light on this issue. It's not about complaining, it's about saying, look, this is kind of the reality that no one's seeing. We're seeing what Hollywood sells us but we're not seeing the reality of millions of people. And we need to be talking to each other because our silence around this really does just keep the status quo in place. I'm not happy with the status quo right now. I think we need a stronger, more equal, more just society.

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We Need to Talk: A Memoir About Wealth — https://amzn.to/3fAaTXU

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