32: Jen Risher | We Need to Talk... About Wealth

Talking about wealth is often uncomfortable—but it’s essential. In Episode 32, Lindsay speaks with Jen Risher about why honest conversations around money matter. Jen shares how openness about wealth can reshape philanthropy, relationships, and our understanding of privilege and generosity.

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Money is a currency. Let’s have taboo conversations for the commonwealth.

“When we don’t talk about something, it tends to loom large and take on a life of its own. When we don’t talk about money we are giving it so much power. Let’s take power back and put the money in its place” Share on X

When it comes to money-related issues, mum’s the word. Talking about wealth right now couldn’t be more charged. Did you know that 8 out of 10 people who are wealthy grew up in middle class or poor neighborhoods?! I didn’t. Have you ever felt bad for the rich? I have. Why? They are human just like everyone else!

There’s a lot of stigma around the issue. This is why I am delighted to talk today with Jennifer Risher, author of the book We Need to Talk: A Memoir About Wealth and initiator of the social giving movement encouraging giving during COVID-19 called #HalfMyDAF. This effort called for spending (donating) the $120 Billion parked into Donor Advised Funds NOW.

So many people go without healthcare, food, housing, and education. Attributing value to socioeconomic status makes talking about money, and wealth especially, taboo. It is that silence that sanctifies us from examining our relationship with money and keeps the status quo in place. When we avoid discussions around money, we stay in our bubble, we remain unaware, and we don’t hold ourselves accountable. That’s why we need to hear people’s stories, understand our own story, and better process our emotions regarding wealth.

A memoir about wealth

When Jennifer Risher joined Microsoft in 1991, she met her husband, and with him became an extra-lucky beneficiary of the dot-com boom. By their early thirties, they had tens of millions of dollars. Today, there are millions of people like her. We Need to Talk: A Memoir About Wealth tells her story and explores the impact of wealth on identity, relationships, and family. Jen wants to help us talk about money as a way to connect, learn, and shake up the status quo.

Life is not fair, but the more we can understand, the better we can address the issues that permeate society. Wealth is isolating and people who aren’t connected — who are estranged — won’t be at their most generous or empathetic. Jen’s story offers an insight into how people handle newfound wealth and the changes that happen in relationships when money comes around.

We Need to Talk About Donor Advised Funds

Donor Advised Funds (DAFs) are like charitable checking accounts—and they are booming in America. Right now, an estimated $120 billion is sitting in DAFs across the country.

But here’s the challenge: while the funds accumulate, distributions often get neglected. Maybe it’s because life is busy. Maybe it’s uncertainty about when or where to give. Or maybe donors simply need more advisors encouraging and guiding them on their philanthropic journeys.

Whatever the reason, Jen and her husband David have a clear and powerful call to action:
#HalfMyDAF challenges donors to move money out of DAFs now—putting it to work in nonprofits addressing urgent issues like food insecurity, education, domestic abuse, and climate change.

Why DAFs Matter to Nonprofits

DAFs offer donors anonymity, which can make it difficult for nonprofits to build relationships with their supporters. And we know: relationships are the heart of philanthropy.

#HalfMyDAF provides that much-needed nudge—encouraging donors to connect with organizations and move dormant funds into active missions.

The impact is real:

$1 million offered in matching grants
$8.6 million moved into nonprofits in just five months

By encouraging action, Jen and David inspired people to give generously, talk openly about philanthropy, and build community through giving.

Talking About Money: Five Steps for Better Conversations

One of the most important takeaways from this episode is how to hold better conversations around money—especially when emotions run high. Jen shares these five powerful steps:

Identify it:
Recognize that money triggers emotions. Notice recurring conflicts tied to financial conversations.
Set it:
Schedule a specific, emotionally neutral time to talk.
Name it:
Acknowledge upfront that the conversation might be uncomfortable—and that’s okay.
Regulate it:
Create a respectful space for uninterrupted sharing. Try giving each person five minutes to speak, then respond.
Resolve it:
Find solutions that build safety and trust for future conversations around money.

Let’s Keep the Conversation Going

Money can be a tricky topic. But when we talk about it—with honesty and empathy—we can create real change.

Tune in to this episode to learn more about #HalfMyDAF, moving funds to action, and building a stronger, more connected giving community.

Key Takeaways:

08:19 – Donor Advised Funds and the dynamic anonymity creates between the person and the nonprofit.

14:07 – We need to talk: Breaking down the wealth taboos and stimulating conversations about things that are hard to talk about.

16:51 – The five steps to engage in conversation and overcome your relationship with money.

21:13 – How to achieve high-value conversations and relationships as a nonprofit and/or philanthropist (and avoid being awkward and uncomfortable around making the ask).

32:11 – What it’s like to talk about something deeply personal and taboo in order to be a change agent (as a book author and a podcaster).

40:22 – What we need to be doing in order to help fight the income gap and how gender roles affect our conversation around money.