Rebecca Fishman Lipsey began her career with Teach For America, working in a public school. The experience brought her to Miami and shaped her focus on education and community development. Her path has not followed a single trajectory: teaching, policy, entrepreneurship, and philanthropy connect through purpose.
“I have loved all the jobs I’m in. I’ve never done them thinking about how it’s going to unlock the next thing… I want to look back and feel like I used my time” she comments.
Miami’s Ongoing Challenge: Local Responsibility
Miami’s diversity is extensive, but many residents still identify with other places. Lipsey views civic attachment as the core issue for the city.
“The biggest challenge… is getting people who live here to lock in and feel a sense of responsibility” she says. The foundation’s work focuses on converting that transience into shared accountability for local outcomes.
Lipsey describes The Miami Foundation as a mirror of the city’s variety and experimentation.
“We’re a really good collab… not trying to be some other community… Do not be afraid to play and to dare” she says.
The organization’s approach is to surface existing strengths, support collaboration, and allow room for trial and change.
Give Miami Day: A Habit of Giving
Give Miami Day is a single-day appeal for donations across causes in the city. It has grown into a local practice of participation.
“Everywhere you look all you see is people being generous, getting involved, and giving back” she says. Last year, the event received 109,000 donations and raised $40 million in one day. This year’s event takes place on November 20.
Lessons from Radical Partners
Lipsey previously led Radical Partners, supporting over 150 ventures. Two lessons continue to shape her work:
- Collect feedback early and adapt before large investments.
- Accept trade-offs and direct attention where it matters most.
Integrating Life and Leadership
Motherhood informs how Lipsey evaluates community needs. She asks whether current conditions are those she would want her children to inherit. Personal balance also matters.
“You don’t give 100%. You give 95%. 5% you need for you. My music – that’s for me” she says. Music serves as her private activity for focus and recovery.
Expressing Leadership Through Style
When Lipsey arrived in Miami from New York, her clothing was mostly black and gray. A board chair advised her to consider how her presentation connected with the city. Over time, she integrated color and expression as part of leadership presence.
“As I find my own power, I allow my personality to come out of my wardrobe” she says.
Her approach is structured simplicity—neutral clothes and distinctive shoes. The shoes, she says, are both functional and symbolic.
“I believe these are yours… I think I do need a POW rhinestone red shoe” she says.
Equity and Local Decision-Making
Equity for Lipsey means directing resources toward people closest to the problem. Data and listening guide how the foundation invests.
“People don’t want a hero. They want to be the hero of their own story” she says.
The goal is to support community actors rather than replace them.
Lipsey notes that women often face shifting perceptions tied to age—being seen as too young or too old. She emphasizes self-recognition rather than external approval.
“If that red carpet is not being rolled for you, you roll that carpet… You belong there and take your seat” she concludes.
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