Learn how Jennifer Risher is breaking the money taboo.
Steph Wagner, National Director of Women & Wealth, sat down with Jennifer Risher, author of “We Need to Talk: A Memoir About Wealth.” As a lucky beneficiary of the dot-com boom, Jennifer’s story reveals the hidden impact of sudden wealth on one’s identity, relationships and sense of place in the world. Today, she is a public speaker and co-creator of #HalfMyDAF, a movement focused on inspiring donors to move charitable dollars from Donor Advised Funds to nonprofit organizations.
We hope you enjoy learning about how we can all improve our relationship with money to unleash our power to make an impact on our families and communities.
LISTEN TO THE FULL INTERVIEW
The following interview has been edited for length and clarity.
Steph Wagner: I’m Steph Wagner, National Director of Women and Wealth here at Northern Trust, and I’m thrilled today to be joined by Jen Risher, author of We Need to Talk: A Memoir About Wealth. Welcome, Jen. It’s so great to have you here.
Jen Risher: Thank you, Steph. It’s great to be here.
SW: Jen and I had the fortune of meeting last month when she came to Chicago to speak at our national Wealth Planning Symposium. And the more that we talked and the more that I learned about her incredible story, it became extremely clear to me that she’s on a mission. And it’s all about moving money away from being this taboo topic and helping people to better understand their relationship with it. And I think most importantly, the why behind that, and to encourage us to have critical and often extremely uncomfortable conversations about money, not only with ourselves, but those that we love. And all of this can really help us to stop giving money so much power and to start seeing it as a tool that we can use to do good and to make a real impact within our communities.
Jen, I think this mission of yours is so powerful and I deeply appreciate the work that you’re doing, especially for women.
JR: Thank you, and that’s very well said. I want to add that while these conversations are awkward and uncomfortable, on the other side of that discomfort and messiness, there really is a sense of relief, a chance to connect, and a chance for us to really step into our power.
SW: Amen. It’s very liberating, no doubt.
JR: It is.
SW: Well, I think it’s very safe to say, and correct me if I’m wrong, that your life’s journey led you to find your passion, which I think makes it even more powerful, and inspired you to write this incredible book. I think it is a must read! It navigates your story of sudden wealth and then exposes the impact that it can have on our identities, our relationships, and really our sense of place in our communities. I would love to start there. Can you share a bit about your story and how all this came about?
JR: Yeah, you know, I got really lucky. When I was 25, I joined a company called Microsoft and I met my husband standing in line together at our orientation. It was in 1991 and I got stock that was worth hundreds of thousands of dollars. David’s stock was worth millions of dollars. It was crazy. Even crazier, years after we first met, we were married and expecting our first child. We were both still working at Microsoft at that time. Then David decided he wanted to go join a small startup that was selling books on the internet. He was the 37th employee at Amazon.com. When the company went public we were in our early 30s, and suddenly we had more money than we could wrap our heads around.
SW: And really in uncharted territory — and all from a little bookstore.
JR: Yes.
SW: I love that story. Let’s dive into it a bit more. When we think about it, it’s all amazing, right? But there were some surprises that came with the sudden wealth that I think might surprise all of us in terms of the emotional component.
These conversations are awkward and uncomfortable, on the other side of that discomfort and messiness, there really is a sense of relief, a chance to connect, and a chance for us to really step into our power.
JR: Yes. We all think sudden wealth sounds amazing. Many of us have thought in the past, ‘What would I do if I had a million dollars?’ And it does sound very fantastical from the outside, but the feelings that actually came with the reality of it didn’t match that glow that I had imagined. I was still me. And that was sort of surprising. Like, ‘Oh, wow, my feelings are still getting hurt, and I still make mistakes, I still have insecurities.’ And it was a shock to suddenly feel like my identity was at stake. Because the way I’d grown up, people with a lot of wealth were sort of ‘them.’ They were kind of ‘those people.’ And I had this idea of who they were. I had a lot of feelings that came up. Did I look the part? Did I look stylish and sophisticated enough to be someone with wealth? And all these emotions were churning around and I really felt like I couldn’t talk about it.
SW: Absolutely. I’d love to go back a bit and talk about how you were raised. Because when we think about our relationship with money, and some of these emotions that get brought up, for many of us most of that stems from the messages that we received as a child — what we saw, what we talked about, and what we didn’t talk about. Can you give us a little bit of insight about that and how you were raised and how it compared to where you were at that moment sitting there trying to navigate this extreme wealth?
JR: Yes, I think we all get a lot of our habits and beliefs around money as kids and the way our parents each approach money. And so, for me, I really grew up with solid middle-class values. Hard work was really important, as well as being frugal and diligent about managing my money well. I remember my first job was picking up leaves off our front walkway. And my dad took these big bags of leaves that I had picked up and we counted and then he put the money into my hand, and I put it in my piggy bank. And I remember going and opening a bank account with my mom, and we would put the money in. I could sign my name. It was all about keeping that money safe and saved. Saving was a priority in our family. It was good to be frugal, and bad people spent to excess. So, I grew up with that sense of work hard, saving your money. That was super strong in me.
SW: So how did your relationship with your parents evolve as suddenly you were on the other side of that? I’d love to unpack that and explore how the dynamics within your family unit changed, if at all.
JR: Yeah, there’s a lot of unpacking to do. It could take years. And it did take years, actually. I grew up kind of wary of the rich. And questions inside me came up like, Was I now something that I grew up prejudiced against? Was I that person? And how was I going to handle that?
My parents and I never talked about money when I was growing up. That was impolite and not dinner conversation. I never learned the skills around how to talk about money, so I didn’t know how to talk about it. I had now become this thing that I had always looked negatively at. And I didn’t talk to my parents about it. I had this assumption about how they were looking at me and it was really awkward, and I felt like, oh, they don’t approve of what I have and that’s painful and they’re not saying anything about this situation that I’m in. I didn’t say anything, and therefore definitely played a role too. I made a lot of assumptions. I think that’s a part of the downside of not talking about money is that we tend to just make assumptions and tell ourselves stories around these things that may not be true. Looking back, of course, I wish we had been able to kind of address some of the things we were all feeling. Instead, we didn’t.
I wasn’t worried that they would like me for my money. I really was concerned that they’d hate me for it, that I’d be judged for it.
SW: And to your point, the silence led to this loneliness, probably on both sides. And then this creation of judgment that may or may not have even been there.
SW: And that can be very damaging to this beautiful family unit, right? Unnecessarily.
JR: Yes, and it’s really powerful. You know, the people that you want to connect with most, that you love the most, you start to feel distance between because suddenly there’s this thing, this elephant in the room, that no one’s talking about.
SW: And it also impacted your friendships outside your family, right?
SW: I’d love to hear about that. You were a young mother when this happened. And as a young mom, suddenly our friends are our everything. They’re our community, these women that we’re having our children with and can talk to and be vulnerable with. I am assuming suddenly that was changing for you, um, at least internally, right?
JR: Yes, I had this new baby and I was in a mother’s group. I felt so connected with those women because we were all feeling some of the same things. We all had the same concerns like, how are we going to get our babies to sleep through the night? And at the same time, I had this other big event in my life and all this new wealth, and I really didn’t want any of them to know. I wasn’t worried that they would like me for my money. I really was concerned that they’d hate me for it, that I’d be judged for it, that they wouldn’t see me as just another mom. Even though I felt like just another mom. So, I spent a lot of time trying to hide it in the name of staying connected. And of course, looking back at that I think, ‘wow, well that’s exhausting!’ How connected was I really if I was not showing up for what was truly going on in my life? But there was a lot of fear of judgement — of people looking at me differently because of the money we had. I didn’t want that. I didn’t want it to exist.
Connections and our friendships are so important to us. And when you can’t show up and talk about these negative emotions and feelings around something that everyone else was viewing as only positive, it ends up feeling like, ‘well, I can’t complain about this.’ And I didn’t feel like I wanted to complain about it. I just wanted to share how strange it felt, how difficult it felt with my parents at the time, how it impacted my relationship with my brother. Was he jealous of what we had? How was he looking at me? Was he looking down at me? I felt all these feelings. A lot stemmed from how I grew up thinking about money. So, it was a lot to grapple with and that’s why I felt like, ‘well, I can’t talk about this.’ So, I looked around like, where’s the book about the real human experience of what this is like?
SW: Well, thank God, you wrote it.
JR: I had to. It didn’t exist.
SW: Exactly. And I think, the zeros are irrelevant. We talk a lot about that often— this has nothing to do with the number of zeros, right? Because it can impact everyone.
JR: Right! It’s not about zeros, it’s about the disparities. An income inequality happens within our families when someone earns much more than someone else or they’re able to buy more. That’s the moment when we need to be talking instead of avoiding conversation.
SW: That’s right. Because that is when we begin to feel isolated. We’ve talked a lot today about our relationship with money — how we were raised, how all that complicates these issues. And then, when things change, it can really trigger feelings of isolation, fear, shame. Shame, I think is a big word here. But it really boils down to the need to do a very important thing — which I don’t think we do enough of — and it’s examining our money story. We all have a money story that we need to dive into, think about, write out. I know you believe this is a starting point for creating conversation and change.
JR: Yes, it is. It was important for me personally to understand my money story so that I could work through it and understand why certain feelings were coming up. Part of my money story was, good girls, good daughters, good people saved their money. And so, my sense of self-worth and self-esteem was built around saving. And so, if I was spending, then I wasn’t good. But then I found myself wondering, wait, what am I saving this for? What’s behind this? Why am I driving around the block searching for a free parking spot on the street and terrified to pay for parking? Is it because it’s going to say something terrible about me? Why do I have this link between my value as a human being and how I’m interacting with money? So trying to decouple those things and get to a place where I feel my value as a human being apart from money.
My mother’s parents grew up in the Great Depression, which really shaped her view of money and wealth. She was all about saving and doing things the proper way. Her parents were part of a bridge club and there was a right way of doing things that she felt that she needed to live up to. This belief trickled down to me. I felt that I had do things just perfectly.
We all know that in relationships, money is one of the big stressors. So, understanding your partner’s money story can really help alleviate some of the stress.
Money wasn’t spoken about in her family because she was a woman. And her mother (my grandmother), didn’t work because she was a woman even though she had gone to college. She met her husband in college and he didn’t allow her to work. So, these behaviors are passed down generation to generation. And on that side of my family, women just weren’t supposed to touch, think about or talk about money. On my father’s side, he had dropped out of school in eighth grade to work. He went to work in a bank. My dad was the oldest of five children and remembers a time in his family when there wasn’t enough to eat. He had to rush to the dinner table to ensure he got enough food. He grew up with the feeling of scarcity and there’s never quite enough. And so that was another piece to why I felt a need to save and be very frugal. Who knows what’s going to happen tomorrow? There’s always a rainy day waiting there. Recognizing those things inside me, even now when the situation is very different, and the feelings that come up around spending, I have to really think about it, think through it, and say, ‘Okay, wait a second. Maybe it is okay to spend a little money here.’
SW: I think it’s all about building self-awareness around it. And as we discussed earlier, being able to have critical conversations with ourselves, really being open and honest with ourselves in order to reconcile things to move forward and to not feel that shame.
I love that you brought up how we all have different money stories and how multigenerational it is because it’s so much tied to how we were raised. Your grandmother’s money story is different than your mother’s, which is different from yours. What about your daughters? I know you have two amazing daughters who obviously have a very different money story, a set of experiences, than you and your husband. I am curious about the evolution of that and the reconciliation of money stories across generations because you’ve each experienced something very different.
JR: We all experience something very different, and yet things get passed down. Parenting is hard. I wish that I hadn’t passed some of the things that I did pass down. I’ve also recognized that my daughters are inheritors. So, they didn’t have the experience that I did growing up. They’ve inherited their money and they are very typical of the inheritor mindset. They have a lot of guilt. They feel, ‘what did I do to deserve this?’ They look around at their peers and they have more, and they feel guilty about it. That is counter to my mission in life of trying to help people really step into their reality and their power and get past feelings of guilt and shame. So, I have work to do with them. And they have work to do within themselves around looking at that and recognizing who they are, coming to terms with their own money stories. And I think this is important for each of us as individuals to come to terms with. Because when you think about it, the more you understand your own money story, the more you have empathy and understanding for someone else’s.
SW: That’s right.
JR: We all know that in relationships, money is one of the big stressors. So, understanding your spouse’s, your partner’s money story really will help alleviate some of the stress. If you understand, oh, they’ve learned that spending is important and buying gifts is a way of showing love, where you had a completely different story, you can recognize their actions and the emotions that are coming up from them, which allows you to really find the connection and talk through things. Similarly, for people who work with people who have money, like advisors or fundraisers, they should really recognize that the person you’re working with also has a money story. So, there’s a lot at play here. And the more we can recognize our own fears and biases and those emotional triggers, the more we can help someone else, see someone else and understand someone else.
The more we can recognize our own fears and biases and those emotional triggers, the more we can help someone else, see someone else and understand someone else.
SW: I am so glad you brought that up because again, part of your mission — and I think the real important component here to success — is communication, right? And without understanding where other people are coming from, you don’t have the ability to think about how you message things.
JR: Right.
SW: How do I have a successful conversation? It doesn’t matter what I want to say, if what I say isn’t going to resonate or be received the way I intend. And so I love that you’re bringing this up because it really is the starting point to having those critical conversations that can be successful and that can help your daughters overcome the guilt and unleash the power that money can have when we use it constructively versus letting it hold us back, being full of shame or guilt or fighting about it or creating stress over it. So, thank you for that, because again, regardless of the actual dollar amount of your wealth, these are issues that resonate across all families, across all friendships, across all relationships. It’s such an important point.
You also talked about women and thank you for sharing that history within your family. Obviously, both men and women have an emotional tie to money that needs to be unpacked. But women in particular really struggle with it. In fact, studies show the number one thing that holds women back when it comes to their relationship with money is shame and embarrassment, the idea that ‘I don’t know enough. I should know this. I don’t know this. I don’t know where to turn.’ Can you talk a little bit about that? I know women and wealth is something that you’re very passionate about, too. What do you think we need as women? What’s going to be part of the solution for us to really create change? Because truth be told, it is a very exciting time for women around wealth. By the end of this decade, we will control $30 trillion. That’s really a lot of economic power that we need to unleash to do good, but we’ve got to start here in order to do so.
JR: Yes, it is an exciting time! There’s a lot of opportunity! And yes, I think it is tricky for women and there’s that ‘shame.’ I want to share that initially my book was called “The Embarrassment of Riches.” So, the embarrassment piece was very prevalent in my story. For women, I think it’s the cultural norms, as well as our gender roles that are pretty deep within us. Those two things come together to make it even more difficult for us. Historically we haven’t been the breadwinners. We haven’t been out there creating wealth. That’s new for us. Although this may sound stereotypical, we tend to be the connectors, the caregivers, the ones that are making sure that everyone feels comfortable and that there aren’t divides. So it makes us feel uncomfortable when money creates conflict. And this can create additional challenges for us to step into that potentially uncomfortable space. And yet I do think we can be leaders in this space if we learn to talk about money.
You mentioned my daughters. How am I going to help them move out of guilt? How are we going to stay connected as a family? How are we going to talk about our values? I’ve been the person in our family bringing us together for family discussions about money to discuss where we all stand and how we’re each feeling. And I think that’s a leadership role that women can play within their families, within their communities. But we need to first get comfortable with it for ourselves. And for many of us, that feels risky because we don’t have experience. At a technical level, we need to be talking about money so that we can gain equity in the workforce. How much are we making? How much am I charging per hour? Get those numbers out there so that we know where we stand and we’re sure that we are equal to each other and to the men out there so that we have the numbers and the information, and we can use money as a tool in that respect.
SW: I absolutely agree. And what you’re referring to is really the core of what we’re building with Elevating Women, which is a community that creates this brave space for us to talk about these issues, to be vulnerable, to share experiences and to learn from experts. So, this topic of money isn’t so taboo. And it starts with the front end, right? The earning, the creating. But equally important is now that you have it, what do you need to know to be good stewards of it? And so, it all comes together. And I really appreciate what you’re saying because at the end of the day, it is the power of community and having that place to share and to talk that will help us and the next generation.
JR: Yes! Community is so important. I have been in groups of women and felt that power of the learning together, and from each other. The support that comes from other peers and groups of women I think is so powerful. So, I appreciate what you’re doing to bring women together because that is what can catalyze us to activate our money in ways that feel really aligned with our purpose and values.
It makes us feel uncomfortable when money creates conflict. And this can create additional challenges for us to step into that uncomfortable space. Yet I do think we can be leaders in this space if we learn to talk about money.
SW: Well, let’s talk about that, because what you and your husband, and ultimately your entire family, has created with your wealth is magnificent. And I think to your earlier point about the role women can play within their families, you were really the driver of exploring the emotional aspect of money and unleashing the power of what your family as a unit could do. And you all have created tremendous impact through your work. And I would love you to talk a little bit about, or rather a lot about, Half My DAF and this movement that you’ve created to deploy money and do something incredibly powerful with it.
JR: Thank you. Yes, and as you know that movement, #HalfMyDAF, didn’t start out as a movement. It really started out as an emotional response. And I often think that’s what we need to tap into. Like, what do we care about? What problem do we want to solve in the world? How are we going to move forward and make a difference? And it was during COVID when my husband and I were sitting in our backyard, and our hearts were going out to nonprofits that were starving for funding at a time when the need was so great. COVID began to spotlight the inequity in our country.
We saw nonprofits were working so hard and then we looked over and saw all this money sitting in Donor Advised Funds (DAFs). In fact, at that time $120 billion was sitting in Donor Advised Funds. These are charitable dollars — you put your money into the Donor Advised Fund, you get your tax break, and then you can move it out over time. It is a good vehicle, but it must be used to do good. This money was sitting there and we were so shocked by that reality.
Since we wanted to help nonprofits we thought, ‘well it’s one thing if we just give directly; but how do we inspire others to join us?’ This was an ongoing conversation that my husband and I were having. We wondered what we could do and ultimately came up with an idea and named it #HalfMyDAF. We created a website and said, “We’re going to put up a million dollars and that money is going to be used as matches for anyone who commits to spending down half of the money in their DAF by September 30.” We started talking to people, we started learning, and we launched it that May. And you know, it’s interesting because there was a moment where I thought, ‘Okay, we’re going to put up a million dollars.’ And just saying that out loud and saying it very publicly is vulnerable. And that’s a moment that can stop people, and I’m so glad it didn’t stop me because I think we need to be more transparent.
Here’s a moment about talking about money. I’m going to do this thing. I’m going to lead in this space. And I’m so glad I worked through that and I did it quickly. But I heard other people, donors who were giving through #HalfMyDAF, tell me, ‘Hey, Jen, my siblings don’t know how much I give to different organizations, and now you’re seeing those numbers and it makes me feel vulnerable.’ But we had a lot of very positive feedback too of like, ‘Wow, we would never be having these conversations around the dinner table with our adult children, talking about our values, talking about where we want to give, moving that money.’ And in fact, that year from May to the end of September, our million dollars turned into $8.6 million out of DAFs and into nonprofits.
SW: Can you share where are you today? Because now we’re three years into this and the numbers are mind blowing.
JR: It is actually year four.
SW: Love it.
JR: It was not something that we had intended to continue. It was not meant to be an ongoing project, but our daughters got involved. That first year, our daughter was sheltering in place with us. She did a lot of the data entry. It was a lot of work to track the gifts and to work with the nonprofits. Our older daughter took that on for the year, too. I mean, this is a parent’s dream come true. At Christmas time, they surprised us with a gift and said, ‘We want to join you in #HalfMyDAF.’ They each have their own money. They each came to us and said, ‘I want to give money towards #HalfMyDAF. I want my money to go to racial justice causes.’ Our other daughter said, ‘I want my money to go to climate and environment.’ So, they helped us shape our thinking with #HalfMyDAF. Initially, we told them to give wherever you want, as long as it doesn’t promote hate speech or gun violence. The second year we also had buckets of money, places where our values were showing up and our daughter’s values were showing up, and so we committed to match extra money to organizations supporting those different areas. We’re now in year four and we’ve moved over 35 million dollars through #HalfMyDAF.
SW: Unbelievable.
JR: Thank you. It’s very exciting and it’s kind of bigger than the numbers too because people are now more aware of this, they’re more aware of the issue, and they’re inspired to give.
SW: I think it is such a shining example of the importance of working through the complexities wealth can bring, having those critical conversations and learning about yourself, sharing that with your family, taking it to that next level of suddenly unleashing this dark shadow and turning it into the massive opportunity that it can create, not only in your community, but look at the impact that you’ve had on so many others and inspired them to do the same.
So again, it’s unbelievable. I commend you for the great work that you’re doing. And I know you’re not done. You’re also focused on helping the next generation of entrepreneurs — female entrepreneurs, especially female entrepreneurs of color and looking at ways to give to them to create impact. You’re truly a change agent and an inspiration to all of us. And I appreciate all the great work that you and your family are doing.
JR: Thank you so much. Well, it has been a journey, and I’d have to say that this is the most exciting part of it, because I do feel so much power around it. I’m no longer wringing my hands around the money and worried about how it’s going to look. I’ve just stepped into it, and it’s been a really wonderful experience. I’m so excited. It feels a lot better, and I think I can have more impact in this space. And you’re right, it’s like looking at our money and thinking, how do I make the change I want to see in the world with this? Not only philanthropically, but through investments. As you shared, I’ve become an investor myself. I’ve invested with four different women of color who are fund managers. I’ve done some angel investing and it’s just, it’s exciting.
SW: I love it. Well, thank you for the great work. And I want to just say and end with it’s a much better use of time than circling around looking for a free parking space.
JR: It certainly is. Thank you. »
Learn more about HalfMyDAF.com and Jennifer's book “We Need To Talk: A Memoir About Wealth”
