Zibby Owens: Welcome, Jennifer and David, to “Moms Don’t Have Time to Read Books.” I’m so excited to have both of you here with me today. Thanks for joining.

David Risher: Thanks, Zibby.

Jennifer Risher: Thanks for having us.

Zibby: This is a dual-purpose interview. The two of you, this power couple who now I know the most intimate details of your life because of Jennifer’s book — I’m almost embarrassed. The book is called We Need to Talk: A Memoir About Wealth, but it’s really also a memoir about you. It’s about your success in life and how things have developed and your relationship and family and struggling with everything from, am I spoiling my daughter by going to Hawaii when she’s eight months old? to all these big and small questions in life. Then David is here, A, as your husband and the central character in this book aside from you, and also because he’s doing such amazing things, as you both are, for reading worldwide. Lots to discuss. Why don’t we start with the book? Jennifer, would you mind just telling listeners who aren’t aware and who might not have gotten the full scoop from my brief summary there what your book is about? Also, what made you write this book? What made you write it? Why now?

Jennifer: Zibby, I’m really lucky because when I was twenty-five, I joined Microsoft and I met David. I also got stock that ended up being worth hundreds of thousands of dollars. Six years later, Dave and I were married, expecting our first child. Dave had started this job at an unknown startup that was selling books on the internet. He loves books. He wanted to try this thing out. It was Amazon. We were in our early thirties. We had more money than we could wrap our heads around. Wealth surprised me. I didn’t find myself in a big, sparkly, private club hanging out and sharing financial secrets. I found myself kind of alone in a strange, silent space where no one talks much about money at all. I felt the resentment of friends. I was worried about raising spoiled, entitled children. I wasn’t sure how to give to family members or how to approach philanthropy. No one discusses these things even though most people are new to these challenges. Eight out of ten people with wealth grew up middle class or poor. I was surprised that wealth felt so isolating. Normally, if I have a problem or a question, I turn to friends. If I want to figure out, should my sixteen-year-old have a curfew? I ask everyone I know. I get their ideas. I hear about their experiences. I get advice. Just talking about something like that is helpful because it lets me know my question is normal, that it’s shared. The same doesn’t happen with money. I couldn’t talk to people about having a lot of it. I thought, I’ll turn to books. I wanted to find a book, but there were no books.

Zibby: Where is the bookshelf for people who have won the lottery? I can’t find the book about this.

Jennifer: I needed that book. Actually, I wrote my book because my story is one I’d want to know about if hadn’t happened to me. I also wrote my book for the millions of Americans like me who have more money than they had growing up or they have more money than many of their friends or they have more money than others in their extended family. I’m sharing my story as a way to help other people understand their own. We have this fairy tale idea about wealth in our heads. The reality feels strange and lonely. I’m not trying to show people how to do rich right. I don’t have the answer for that. I am offering up this story that hasn’t been told.

Zibby: I feel like you came in, also — sorry, I hope I didn’t interrupt you. You came in with this bias. I feel like your family was particularly, not anti-wealthy, but there was such a judgement attached to spending anything. I feel like you had such a chip on your shoulder. Maybe not everyone coming into wealth is that almost disdainful of it or, I can’t enjoy this house or I can’t get a connecting flight or whatever it was. I feel like you had a particularly strong background against it. Then when you found yourself in it, you had to do a lot of mental work. It was like cognitive dissonance in a way.

Jennifer: Absolutely. To become something that you’re biased against is tricky. I had to really work through that. I do think that we have a very narrow and incomplete view of wealth in our country. We see the stereotypes. We know the Kardashians and the Real Housewives and the men of Wolf of Wall Street. Of course, we’ve heard of Jeffery Epstein or the parents who illegally try to get their kids into schools that they’re not qualified for. We see these stereotypes. I don’t think I’m the only one who has this view of what wealth is all about. It doesn’t look or feel like what Hollywood sells us. Eight out of ten, like I said, people with wealth grew up middle class or poor, so they are you.

Zibby: I feel like so many people would be like, really, so it’s hard for you to be suddenly wealthy? I’m really sorry about that. That’s why you can’t get a normal conversation going about it. It’s something that people would really like to have even if there’s a bias. It’s a woe-is-me problem. Woe is me. Should I go to Aspen or not? These are the tough questions. I think people are very quick to mock it and not understand it. Then there left a big hole for your book, so there you go.

Jennifer: I think there’s a reason this book hasn’t been written. It’s because of that. I think it’s important to start conversations. No matter how much you have in your bank account, if you have parents, if you have a partner or siblings or friends, you probably know that money is uncomfortable to talk about. You probably have faced that awkward money moment or you have some money issues hanging over your head. It’s emotional. These emotions are universal. No matter how much you have, we have a lot of fear. It’s fear of being rejected, fear of hurting other people’s feelings, fear of not measuring up or of sounding unknowledgeable. We all have money shame and money guilt. We all have that money story that starts in childhood.

Zibby: David, I don’t want to leave you out here. I have all of Jen’s views of her family and her wealth and all this stuff and some of yours. What was this whole experience like for you? Do you share the, let’s talk about it, let’s let other people in, mission of Jennifer’s right now? How do you feel?

David: For sure, the answer is yes to that question. I do. My growing up was different. I didn’t grow up with a lot of money myself. In fact, I was raised by a single mother. Our big event for the week was going to the library and coming out with a big stack of books. That’s how we explored the world. It obviously has something to do with what I’m doing now. For me, there’s probably less emotion, in a sense, tied up. What my mother would say is, we’re not poor, we just don’t have any money, just a neutral statement. I didn’t have this kind of bias coming in. At the same time, I had no preparation for what we’ve gone through at all. As Jen said, this is the book I would’ve looked for in the bookstore if it existed. Instead, she had to write it.

Zibby: Wow. By the way, I used to work a company called Idealab. I don’t know if you knew it. It was a big deal in 2001 for a hot minute. I had a moment with stock options because I was the twenty-fifth employee. All of a sudden, I was like, oh, my gosh, this is going to be amazing. I’m going to have this huge pile fall into my lap. It didn’t happen. When you were saying how people had the stock price in the office, checking all the time, that sort of became the culture of some of the operating companies. Anyway, I don’t even know why I bothered sharing that. I want to hear about the new nonprofit and #HalfMyDAF and all these things that you guys are doing to change the world, Worldreader and everything. When did the nonprofit element, giving back, start bubbling up in your lives? How did it come to this?

David: It’s something we can probably both talk about. We have maybe a little bit different perspective. Neither one of us really grew up in a family that gave a lot of money away. We didn’t have any money to give away. Jen’s parents weren’t really wired that way. For us, Jen talks about this, our first philanthropy was our children’s school asking us for donations and these sorts of things, which, looking back on it, are fine on-ramps, but it’s kind of incremental. It’s not really going to get you over the hump. About ten years ago, we decided to spend the year traveling around the world with our children, with our two daughters. We have two daughters. At the time, they were very young. We were their teachers, which is a whole separate experience, just infuriating and fantastic and everything you can imagine. We also spent every afternoon and often entire days or longer working with them doing service work. We taught at a school in China for a couple weeks, taught English there. We helped paint a house and actually helped someone buy a house in Vietnam and so forth. Along the way, we were reading. That’s a separate story about Worldreader. I think both of us at that point were looking for a little bit of the next thing. I, in particular, was very much looking for the next thing. I’d been at Amazon for many years. Again, I can tell you the story of the beginning of Amazon separately if you’re interested.

Zibby: I would take that.

David: You got it.

Zibby: Finish this one.

David: Maybe I’ll tell you just the beginning of Worldreader which will help tie a couple threads together. We actually ended the trip in Ecuador. We were at an orphanage. It was a girls’ orphanage. Our daughters had volunteered. We had the spent the day working with the young women there. As we were walking towards the exit of the orphanage, the woman who ran the orphanage was looking around. I was too. I saw a building with a big padlock on it. I asked the woman, “What’s going on with that?” She said, “That’s our library.” Here, my ears are perking up because I’m the library kid. I wasn’t good at a lot as a kid, but I knew something about the library. I said, “Why is it locked?” She said, “Look, the books take forever to get here. They come by boat. Often, by the time they get here, they’re not very interesting because they’re out of date or maybe they started out as being someone else’s almost trash books type of thing. The girls just aren’t very interested in that anymore.” I said, “Gosh, that doesn’t sound good at all. Can we take a look inside?”

She said, “I think I’ve lost the key to that place.” When she said that, now we’re looking at our two daughters. Each of our daughters has a Kindle because of my Amazon background. We use that to read around the world. Every place we went, we would read books that were local books. I just said, this is crazy. One thing led to another, and we started Worldreader with this notion that everyone can be a reader. Readers build a better future. They’re healthier. They’re more prosperous, more empathy. If we can get a billion people reading someday, this world will be a better place. That’s been what I’ve been focused on these last ten years just as Jen has been focused on for fourteen years, writing this book about money and philanthropy and doing more in the world. It’s been a really interesting both parallel path, but then paths which keep crossing in all sorts of fun ways.

Zibby: You must have really great, inspiring conversations at the dinner table about what you guys have been doing during the day. That’s pretty awesome. Insider look at the formation of Amazon, I’ll take a snippet of that if you’re offering it.

David: For sure. All I can say there is — you were the fiftieth employee at Idealab.

Zibby: Twenty-fifth.

David: Twenty-fifth, so you know what it’s like to be part of a company that’s still figuring out what it’s all about. I was number thirty-seven at Amazon. At the time, it was, as Jen said, a tiny little internet bookstore. We had sold $15.6 million of books in 1996. In 1997, after some conversations with this crazy guy named Jeff Bezos who actually literally called me one day checking the reference of someone who used to work with me when I was at Microsoft — anyway, joining this company, he had this huge vision of, I want to be the place where you can find and discover anything you want to buy on the internet. That was his early vision. Maybe, if we’re lucky, we’ll get to a billion dollars by 2000. I just said, look, how could I not do this? It’s technology, which I’d grown to love at Microsoft. It’s books. There was a bookstore. We could become earth’s biggest bookstore. That was our tagline at the time. We could maybe do something that really did change the world.

It was exhausting and crazy. Frankly, we didn’t know what we were doing half the time. We almost ran out of money a couple times. Again, it’s probably a whole separate podcast. All I can say is that from the outside today, Amazon looks like this incredible machine. I will tell you, when you’re employee number thirty-seven and you’re literally putting down the train tracks as the train is just barreling down the tracks, it’s pretty frightening. Last thing I’ll say, my mother, she would call me and she would say, “David, what have you done? Why have you left Microsoft to go to this crazy thing?” The papers would be calling us Amazon.bomb. That was the thing. Anyway, no one knew why I’d made this crazy decision. I just said, “It was kind of about books, kind of about reading, and almost a passion for me to see if this was going to work.” Luckily, it did.

Jennifer: At that time, people weren’t going to their computers to buy things. I was like, oh, my gosh, who’s going to go to the computer to buy a book? Then he was going to add music. He was going to add toys. I’m like, no one is going to go to their computer. Luckily, someone else had a better vision than I did.

David: Actually, Jen was a huge advocate of my going. We were just about to have our first daughter. It was kind of crazy. People would say, maybe you should just have one child at once, not have a child and a . It worked out.

Zibby: Wow. That’s nuts. What a story. I feel like, though, the startup life and the parenting life, you’re probably up at all hours in both cases. It must have been a nice symbiotic relationship.

David: Right. Neither one of us slept for about seven years. It was fine.

Zibby: Who needs sleep? Nobody needs sleep. Jen, in your book, I found it really interesting that interspersed with all of the personal stories and the thought-provoking issues you brought up, you had little pages with discussion questions as if you wanted us to stop and literally — little conversation starters. All right, I better stop and talk to my husband about what about the parents about Emily’s new independent school, what are they doing with each other? and all the rest. Tell me about putting in the questions at each chapter, and not even bullet points which I feel like other books do, but almost like reading book club questions as you go. Tell me about that.

Jennifer: I do want it to be a conversation starter and get people talking about money. I talk about private school auctions and private jets. I talk about the luxuries money can buy. I also really take a look at the human aspects and the emotions that arise. Even though the specifics might be different for people, I think people can relate to my stories. I’m hoping that they can understand their own in a new way. Those questions really are prompts to get people to — like you reading it with your husband or giving it to your parents or giving it to your sibling or giving it to a good friend. Then it becomes the catalyst for conversation. It makes it easier to start those conversations. I’d love for people to use those questions not only to think about for themselves, but to share and start these many conversations that are so needed, start them happening. I think my book is the ideal book club book. It’s not easy. I always tell people, this is really, really uncomfortable. I’m sort of inviting people to get uncomfortable. In a book club, for example, it could be like, let’s acknowledge, let’s give each other permission to fumble around, to get it wrong, to get messy. That’s what we’re going to be doing together. If you can create that safe space, it really can bring people closer. I think on the other side of those fears is a real connection, a sense of relief, and then a chance to really learn from each other and collaborate.

Zibby: I have to put you in touch with — have you heard of Emmanuel Acho? He started something called Uncomfortable Conversations with a Black Man. He’s doing all of that about race. Now he has a book coming out, I think this week, that Oprah is helping publish. He’s a big deal. He’s only twenty-nine.

Jennifer: Wow.

Zibby: I know. I know. I know. Let’s put that annoying fact aside. He literally was saying the same thing. You need to feel a little uncomfortable. You have to have a conversation that gets you out of your comfort zone. That’s how we make change. You’re doing it about wealth. He’s doing it about race. Now we need somebody about uncomfortable gender conversations. I can do a whole panel.

David: That’s a great idea. There’s not a lot of examples of people growing without a little discomfort at some point. There just aren’t. That’s what Jen’s really trying to do, is push you into that zone. Then hopefully on the other side, there’s a better connection.

Zibby: It’s like working out. It doesn’t feel good, necessarily, but afterwards, you feel — I mean, sometimes, as I hobble around today. Sometimes you feel better. What do the two of you think about how much anti-wealth sentiment there is in the United States right now? I feel like being wealthy is the worst thing you could possibly be. So many, even, politicians and everybody want to take wealth away and redistribute it. What is your view on all that?

Jennifer: I do think it’s a huge problem. I think maybe it’s the biggest problem our country is facing, this disparity. There’s a lot of resentment. I don’t think the resentment helps anyone. It doesn’t help those who feel it or the people on the other side. When there’s a huge and influential segment of the population that isn’t talking to each other and who feels attacked by this and isolated, it’s not making them empathetic or generous. We need to start closing this gap. Our silence, it has a lot of power. It helps keeps the status quo in place. I’m hoping to get conversations going that can shake things up, help us recognize our own privilege in a new way, help us feel more accountable through conversation, help us collaborate. We have the power to do amazing things and help bring this country together. It’s what we need right now, to be united. To shy away from the resentment and the huge disparity I think is not a service to anyone. People are going without housing, without healthcare, without food. There’s an education crisis. This is the moment that we need to face this. If we’re just going to turn our back or pretend it doesn’t exist or accept it, that’s not okay with me.

David: Just to add super quickly, just like growth doesn’t come without some vulnerability and awkwardness, I don’t think change comes through shame. It doesn’t work. That’s not helpful as a country. It just doesn’t work.

Zibby: What do you think about the fact that so many of the people — I shouldn’t say so many. See, I’m having an uncomfortable conversation in my own head. What do you think about the fact that — if given the choice and you said, do you want a million dollars? most people would be like, sure, hand it over. They’re talking on one side about how it shouldn’t be that way, but if they were to have that happen to them, they would gratefully accept it, perhaps. Not to get too political, but obviously, there are societal issues. Whose job is it to redistribute that wealth? Is it the individual, or is it from the government? I don’t know. What do you think?

Jennifer: I think philanthropy’s wonderful. I think we should all be filling that responsibility, but it’s a drop in the bucket compared to what needs to happen. It needs to happen at a governmental level, policy level. We need healthcare for all. We need to ensure that there’s a strong social safety net for people. I don’t want to live in a society where people are living on the street. That’s a disaster to me. We need a huge structural change. I’m very thankful for our new leaders.

Zibby: Me too. I’m very excited. I’ll air this later, but we’re talking now right after this historic, exciting weekend. I feel like I’ve been bouncing around my house or something. Just so much optimism right now, so much excitement. I’m so ready for it, which is great. Wait, there was something I wanted to ask about wealth. Oh, I wanted to know how you’re handling your daughters at this point. In order to not spoil them, today, what is your approach to parenting without spoiling? What are the rules?

Jennifer: The groundwork’s already been laid. I think it happens early. I don’t think it’s a conversation. It’s living your values day to day, week to week. They’re watching you. Kids see how you interact with other people. They see how you make decisions, what you prioritize. Even just thinking about going into the grocery store with your kids, what do you do when someone cuts you off and takes the parking spot? How do you react? Are you deserving of that parking spot? Do you accept, maybe they’re in a rush, let’s find another one, it’s okay? Going into the grocery store, it’s an opportunity to show your values. Are you choosing things because of the value they have or the price? How do you make decisions? How do you make choices? That’s an opportunity for teaching your kids too. When you go to the meat counter, how do you interact with the man on the other side? Are you gracious? Are you thankful? Same with checking out. All these small details add up. I think that’s what kids really — how they learn is through watching us. It’s about not only values, but our attitude. A sense of gratitude is really important. Even if you’re traveling to amazing places, if you don’t take things for granted, if you show appreciation, all these things are important. You need to walk the walk, and your kids will learn from that.

Zibby: How about entrepreneurial ways versus not? Are you trying to imbue that as something that’s — maybe just by modeling your kids absorb this. Being a Silicon Valley family, perhaps it just goes without saying. What do you think about entrepreneurship in the family?

Jennifer: I want both of our daughters to find themselves and follow their own path and figure out what’s right for them. We’re modeling what’s right for each of us and as a couple. Now they’re in their early twenties. This is their moment to find their own path and find their own passions and find out where they can make their impact and difference in the world. I want to support them to be their best selves.

Zibby: Just putting my own two cents into your parenting, I think that even though they’re in their twenties, there’s still a lot of parenting left in terms of —

Jennifer: — Oh, yeah.

David: There is.

Zibby: Especially in terms of the financial side of life. I think back to my twenties. I feel like my parents were like, okay, she’s good. She knows. We can’t spoil her. She’s off on her own. Now that I’m in my forties, I’m ready to go. I don’t think I was in my twenties, necessarily.

Jennifer: No. I realize this more and more. Especially, this is where the wealth gets layered on. I’m reading a really wonderful book by James Grubman called Strangers in Paradise. It really talks about the stereotypes of wealth and the attitudes that we both brought to wealth, which is middle-class attitudes. Those served us well, but now we have to think about how to use our wealth in society and with our kids. It’s more inclusive. It’s more interdependent. It’s starting those conversations. We have started to have family conversations and talk about our values and our mission as a family who has this incredible resource. How do we make sure we harness that for good in the world and that our children buy into the philosophy that we’re doing this as a family? That is a piece that, it’s in process right now. It’s a big question, and a big question for anyone who’s come into more money than they had growing up. The big worry, of course, is initially, am I going to spoil my kids? Are they going to be entitled? Are they going to be ambitious and motivated? I feel like we’ve checked that box, but then there’s this whole new, how are they going to be as people, as stewards of wealth in the world?

David: Sometimes it’s just better to be lucky than smart. The fact that we started Worldreader ten years ago — at that point, they were in fourth and sixth grade or fifth and seventh grade. They were young at the time. I think that’s right. They’ve had ten years to watch how to steward not just the wealth side, but how you spend your life side of things. Sometimes people ask me about philanthropy and rolling up your sleeves and starting a nonprofit. My basic advice is, do it, and do it earlier than you think you should. Just get into it. First of all, it takes some time to get halfway good at it. Here we are ten years later, and it still feels like a work-in-process, for me at least. Also, it gives your kids and your whole family a way to experience it over a long period of time. As Jen was saying, it’s not just about that. People want to diminish these sorts of things as a one — what does the talk look like with your kids about money? It’s not like that. It’s years of experience and watching and absorbing. I agree. Our older daughter, actually, was just up here for dinner a couple days ago. She actually brought up wealth herself and the relationship that she has with her boyfriend and so forth. She’s twenty-three, so it’s still happening.

Zibby: That’s a whole nother thing. That’s another podcast. What advice would you both have both to aspiring authors having written this book — I’m sorry we didn’t talk a lot about your process. I’m interested in all that. Next podcast. Advice to aspiring authors and then advice to people who really want to use their wealth for good, both.

Jennifer: Aspiring authors, have a lot of tenacity. Keep going. I really enjoyed the process of writing. I found it fascinating as a puzzle. How was I going to piece all these pieces together? How was I going to talk about money in a way that wasn’t off-putting or offensive? I had those pieces to wrestle with. I have been rejected so many times. Believing in yourself, believing in the process, and just keep going. You can do it.

David: That’s good advice.

Jennifer: It took me many, many years, so I’m very happy to have it out in the world.

David: On the putting money to work for good, I would say it really starts with looking in the mirror and thinking to yourself, what do I really care about? It’s so easy to get confused. People ask you, if you have money — even if you don’t have money, people ask you for things all the time. You have to remember that’s a difference sometimes between what they want and what you want. If it comes to doing this sort of work — Worldreader now, as I say, we’re ten years old. We’ve reached fifteen million kids. We’re using technology and local books all around the world. Actually, today — this is fun. I know the podcast will air in the future. Today, Monday, November 9th, is the day we’re announcing that after ten years, we’re finally bringing our program to the United States to help vulnerable communities here in the United States. That’s going to have huge ripple effects on the organization. It’s hard work. It’s hard. Running a nonprofit is not easy, and doing good in the world, whatever that looks like for you. These are big problems, the problem of literacy, the problem with the environment, the problem with, pick your favorite. You better care about it a lot. If you don’t care about it a lot, you’ll give up too fast. If you give up too fast, you’ll get nothing done.

Zibby: That is true. Nobody ever won the race they didn’t go on, or whatever that expression is. Thank you both so much. I really appreciated hearing your story from the proposal at dinner to now. Thanks for letting the rest of the world in on your lives and trying to help others in the many ways you do. If people want to support Worldreader, David, how would they do that?

David: They go to worldreader.O-R-G, worldreader.org, on your phone or on your computer. Come on in and take a look at what we’re doing. We’d love to have all the support we can get. It’s the only way we’re able to do our work.

Zibby: Amazing. Great. Thank you so much.

Jennifer: Thank you, Zibby. Really enjoyed it.

David: Thank you, Zibby. Super fun.

Zibby: I’ll send all the lottery winners your way. You should just put it in the convenience stores. If you win, here’s the book.

David: It’s the ticket.

Zibby: Just a thought, marketing opportunity. Bye.

David: Thanks, Zibby. That was a lot of fun.