Q&A: Unlocking Financial Futures with Cary Carbonaro & Ashley Leftwich

Q&A: Unlocking Financial Futures with Cary Carbonaro & Ashley Leftwich

Ashley Leftwich: Cary, you’ve built an incredible career as a CFP professional, an MBA, a Managing Wealth Advisor, and a Women and Wealth Ambassador. You’ve served as a CFP Board Ambassador, were ranked in Investopedia’s Top 100 Most Influential Advisors, named Investment News’ DEI Trailblazer of the Year, and were the only woman appointed to the Nasdaq Index Advisor Council in 2024. What drives your commitment to financial empowerment?

Cary Carbonaro: Thank you, Ashley. My passion has always been to help people, especially women, understand money and feel confident managing it. I believe money equals power, and women need more of both. We’re approaching a massive shift: by 2030, women are projected to control two-thirds of the nation’s wealth. That’s about $30 trillion. But most women aren’t prepared for that responsibility. They’re often intimidated by money or assume someone else will manage it for them. That mindset needs to change.

Ashley: What’s the first step toward that change?

Cary: Step one is realizing that no one else is going to take care of your money. You have to own it. That mindset shift, taking responsibility and learning the basics, is the foundation of financial power.

Ashley: You speak the language of numbers. My background is in math and a favorite concept I share with students is compounding. How do you see financial literacy shifting behavior?

Cary: It’s everything. Compound interest is the eighth wonder of the world. When students see how money can grow over time, it changes their mindset. I tell them: if you invest early, that money can outgrow anything you’ll earn from your job. That’s real power.

Ashley: Your new book, Women and Wealth: A Playbook to Empower Clients and Unlock Their Fortunes, offers practical guidance. What do you want financial professionals to understand when serving women?

Cary: First, women are not a niche—they’re a powerhouse. Somehow the industry still tends to frame women as widows or divorcees, ignoring the full lifecycle of women’s financial needs. My book gives practical steps on how to better serve women. It starts with communication, no more sports metaphors, no jargon. Just answer the real question: “Am I going to be okay?”

Second, active listening. Know who your client is as a person. People don’t care how much you know until they know how much you care.

Ashley: What advice do you have for students or early-career professionals?

Cary: I like to say ABY: Always Be Yourself. Everyone else is already taken. That mindset has guided my entire career. I never followed a traditional path to build my client base. Every client I’ve ever had has come through organic growth, just by putting myself out there and staying true to who I am.

Be confident in what you know, and be brave about what you don’t. Find a mentor, especially in this industry. It’s getting better, but women still face unique challenges. That’s why mentorship programs are so important.

Also, protect your reputation. Your integrity is everything. Do what you say you’ll do. And then, when possible, go beyond.

Ashley: Can you give an example of what overdelivering looks like?

Cary: In our office, we have a 24-hour response rule. If a client contacts us, they hear back within 24 hours—usually it’s five minutes. If a client doesn’t hear from us, they assume something went wrong, because that’s the level of consistency we’ve built. We once had a client say they hadn’t heard from us, and it turned out they’d sent the message to an old email address. But they knew that silence was unusual for us. That’s the kind of trust that builds lasting relationships.

Ashley: What’s at risk if people, especially women, don’t take control of their financial lives?

Cary: I can’t tell you how often I see women come to me only after a crisis—divorce, death, job loss. They wait until it’s raining. I want women to come when the sun is shining, when there’s space to learn and plan. In over 90% of cases, women will be responsible for their finances at some point. Don’t wait until you’re forced to deal with it. Start now.

Ashley: What a great conversation; do you have final thoughts to share?

Cary: Rock The Street, Wall Street is doing essential work, and I was proud to feature your organization in my book. You’re meeting students at the right time. Financial education is freedom. And when you add confidence to that knowledge, you unlock futures. For students: Be curious. Be consistent. And above all, be yourself.

Ashley: Cary, thank you for your time, your wisdom and your generosity. We’re proud to feature your work and grateful for your support.

Cary: Thank you. It’s an honor to support RTSWS and the next generation of financially empowered leaders.

See the full conversation here:

CFP Board Power Women Design Summit | New York, NY

CFP Board Power Women Design Summit | New York, NY

Rock The Street, Wall Street was honored to take part in the CFP Board’s inaugural Power Women Design Summit, held in New York City. This high-impact gathering convened leaders from across the financial planning profession to explore bold strategies for attracting, retaining and advancing women CFP® professionals.

Founder Maura Cunningham joined a panel discussion titled “Women and the Financial Planning Ecosystem: The Path to Success,” alongside Phuong Luong, CFP® and Kamila Elliott, CFP®. Moderated by Susan Reilly Salgado, Ph.D., the conversation highlighted the importance of early exposure to financial planning, mentorship, and inclusive career pathways.

A highlight of the event was connecting with longtime RTSWS friend Cary Carbonaro, CFP® Professional, MBA, and celebrating her new book, Women and Wealth: A Playbook to Empower Clients and Unlock Their Fortune. Cary’s earlier book, The Money Queen’s Guide, was shared with RTSWS students in past cohorts and helped spark vital conversations about financial independence and long-term planning.

The momentum continues this summer, as RTSWS CEO Ashley Leftwich leads a virtual fireside chat with Cary Carbonaro through our Career Center, offering students and alumnae firsthand access to her expertise and career journey.

Special thanks to CFP Board for creating a space dedicated to action and progress and for inviting RTSWS to be part of the movement to expand opportunity in financial planning.

CFA Institute CareerFest 2025 and CFA Institute Live | Chicago, IL

CFA Institute CareerFest 2025 and CFA Institute Live | Chicago, IL

Rock The Street, Wall Street was proud to join global leaders at CFA Institute CareerFest 2025 and CFA Institute Live, where over 1,400 attendees from 70+ countries gathered to explore the future of finance.

Our CEO Ashley Leftwich and COO Johannah Mullenix represented RTSWS, engaging with university students, alumnae, and industry professionals while spotlighting our expanded Career Center. The Career Center continues to grow as a resource connecting students to internships, early career opportunities, and real-world financial insights.

A highlight of the event was RTSWS alumna Alinda Li’s Lightning Tent Talk. Alinda, a Chicago program graduate, shared her journey from high school student to University of Michigan alumna to Equity Research Associate at William Blair. Her story was a powerful reminder of the impact of early access to financial education.

We also celebrated the many RTSWS supporters featured in panels and sessions, including Wylie Tollette (Franklin Templeton), Blair duQuesnay (Ritholtz Wealth Management), and Heather Brilliant (Diamond Hill), among others. Their insights helped elevate discussions on education, ethics, client relationships, and evolving investment strategies.

Special thanks to CFA Institute and event lead Katharine Warren for hosting a high-impact event that continues to raise the bar in professional development and financial education.

Rock the Street, Wall Street’s Woman of the Year Luncheon

Rock the Street, Wall Street’s Woman of the Year Luncheon

RTSWS-Woman-of-the-Year-logo-2

Honoring our visionary Founder
Maura Cunningham as
RTSWS 2025 Woman of the Year

About this event

The RTSWS Woman of the Year Luncheon will bring together industry leaders, sponsors, and supporters to celebrate Maura Cunningham’s contributions and the organization’s ongoing impact. Looking ahead, RTSWS plans to rotate the Woman of the Year event across its cities.

Date
Thursday, March 27

Time
11:30 AM – 1:30 PM

Location
Richland Country Club
1 Club Drive
Nashville, TN
37215

Awardees

Maura Cunningham RTSWS Founder and CEO

Woman of the Year

Maura Cunningham

RTSWS Founder & Executive Chair

Anders Hall

Champion of the Year

Anders Hall

RTSWS Chair of the Board &
Vanderbilt University’s Vice Chancellor for Investments & Chief Investment Officer

Sponsors

Presenting Sponsor

Event Sponsor

Event Co-Chairs

Ashley Leftwich RTSWS CEO

Ashley Leftwich

CEO
Rock The Street Wall Street

Keri-McInnis

Keri McInnis

SVP
Pinnacle Financial Partners

Your Impact

As a supporter of financial literacy, your participation helps expand access to Financial & Investment education for high school girls. RTSWS students are 5x more likely than the national average female university student to major in finance and related fields, breaking barriers and redefining the future of the industry.

RTSWS at the Franklin Templeton Retirement Innovation Initiative

RTSWS at the Franklin Templeton Retirement Innovation Initiative

Date: March 5-6, 2025
Location: Tampa, FL

RTSWS is proud to share that our Founder Maura Cunningham will be speaking at the Retirement Innovation Initiative Annual Meeting, a gathering of industry leaders dedicated to shaping the future of retirement in America. This event fosters collaboration, innovation, and strategic discussions to improve financial well-being across all life stages.

Our Founder will join experts in discussing industry advancements, policy influence, and financial empowerment. Stay tuned for insights from the event as we continue working toward a stronger financial future for all.

RTSWS x Citadel Securities Event Demystifying Careers in Finance

RTSWS x Citadel Securities Event Demystifying Careers in Finance

Join us in the first week of March for an engaging event designed to connect RTSWS students & alumnae with finance professionals from Citadel Securities.

Highlights:

  • Reception: A chance to meet RTSWS peers and Citadel Securities team members.
  • Panel Discussion: Insights from Citadel industry professionals about careers in finance.
  • Networking Sessions: Small group conversations with experts to practice introductions, ask questions, and gain valuable advice.

Don’t miss this opportunity to learn, connect, and take the next step in exploring the world of finance!

Location
New York
Audience: RTSWS High School Students & Alumnae in the New York metro area