By Madison Lucchesi
A Boston-based mother-daughter duo wants to change how women talk about money.
Deborah McLean started Wine, Dine and Talk Money with her daughter Carlyn O’Leary last year to teach women that talking about money isn’t rude, it’s a tool.
“I want women to be able to have the confidence to join money conversations the same way that men do,” said O’Leary is a full-time software engineer.
O’Leary and McLean found that women don’t discuss their finances due being taught it is shameful and that shame is holding women back from making financial gains, they said.
“Before we started this, I would have conversations with my friends about, kind of, surface level stuff, but … we would never go into how much are you actually making or what stocks are you investing in?,” O’Leary said.
McLean came up with the idea for Wine, Dine, and Talk Money 15 years ago while working in finance. Although she maintained ownership of the domain name, McLean never thought the idea would come to life, but it did when her and her daughter recognized the women in their lives were having similar financial struggles.
“Our friends, although they were at very different stages of life … felt very disconnected from the financial system,” said McLean.
Due to this, O’Leary decided to bring her friends together at her Boston apartment with a financial expert, or “Money Mentor,” to discuss the basics of finance without giving financial advice.
“It was all about bringing women together and creating safe spaces for them to talk about money,” O’Leary said.
Following the first event, their friends wanted to host financial events and the circle continued to grow.
“We basically have wine nights with your group of friends and then bring in a financial expert,” O’Leary added.
Now, Wine, Dine, and Talk Money hosts a monthly meeting for about 30 people at Remnant Brewing in Cambridge, such as a charm bar event to build confidence or an investing 101 brunch.
“We want money conversations to be fun,” O’Leary said.
The confusing language around finance can make money conversations confusing.
“We want to take that complexity and really make it accessible and do that through conversation, not panel discussions or presentations, but really getting to the questions women actually are holding in and need to ask,” McLean said.
To do that, Wine, Dine, and Talk Money’s Money Mentors teach the basics, including high-yield saving accounts, 401Ks, Roth IRA, and investing.
O’Leary said, “A lot of it is, kind of, just breaking down the more simple stuff because that’s what people aren’t taught and what they’re embarrassed to ask because they feel like they should already know those things.”


