Welcome back to Don’t Retire… Graduate! In today’s episode, we’re deep diving into the power of money conversations—why talking about your finances is crucial, and how it can serve as the foundation for a life of financial independence and fulfillment. Joining me is Skyler Fleming, financial coach and host of the “Money Talk with Skyler Fleming” podcast. With over 150 episodes under his belt and firsthand experience working his way up in a credit union, Skyler has become an enthusiastic advocate for breaking the taboo around discussing money and making finance approachable for everyone.

During our conversation, Skyler and I explored how simple, honest conversations can be the gateway to better financial habits, awareness, and ultimately, confidence. Skyler shared his journey, from fielding frustrated calls at a credit union to helping everyday people master their money both one-on-one and through podcasting. We unpacked his signature “seven money talking points,” covering everything from emergency funds and tracking your cash flow to the big philosophical questions about debt and financial goals. We compared coaching versus planning, debated the age-old question of whether or not to pay off debt early, and dove into how technology and automation can make managing your finances easier and less intimidating.

We also discussed mindset shifts through each life stage—why younger folks might want to maximize cash flow and debt leverage, while those closer to retirement may crave the security of being debt-free. Skyler and I both underscored the importance of not just focusing on retirement, but also on all the fun and meaningful goals that happen along the way: dream vacations, supporting your community, or funding your kids’ education. Ultimately, whether you’re in a partnership or on your own, we talked about building your own “money buddy” system for accountability and growth.

5 Key Takeaways:

1. Start Money Conversations Early and Often: Breaking the taboo and having simple, honest money talks—whether with a partner, friend, or coach—can demystify finances and set you up for success, no matter your starting point.
2. Master the Seven Money Talking Points: Skyler’s framework covers crucial questions: your emergency strategy, how you make, spend, and save money, your approach to debt, what you want your retirement to look like, and your big, aspirational financial goals.
3. Automation and Tracking Are Allies: Whether you love spreadsheets or apps, regularly tracking income and expenses—and leveraging automation—can take the pain out of budgeting and ensure your money goals stay on track.
4. Debt Decisions Are Personal: The question of paying off debt isn’t just about numbers; psychology and life stage play huge roles. Make debt payoff decisions based on your comfort, goals, and current opportunity costs, not just the math.
5. Design the Life You Want—Not Just a Retirement: Planning isn’t limited to the finish line of retirement. Identify and segregate funds for your “big money goals,” and build systems (and buddies!) to stay accountable and intentional every step of the way.

Join us as we explore how a little financial transparency and proactive planning can empower you to live with passion and purpose—today, in retirement, and every step in between. Don’t forget to subscribe, rate, and share this episode with anyone eager to have their own “money talks” and transform their financial future!

1. Representation Matters in Finance: Manny highlights the visible lack of diversity in financial planning, and how seeing few role models in the industry can limit a young person’s belief in the possibilities for their own career.
2. The Power of Exposure and Mentorship: Manny’s journey was shaped by mentors and chance encounters—emphasizing that if you don’t know a career exists, you can’t prepare or aspire to it. Intentional outreach and speaking at schools can create these vital opportunities.
3. Apprenticeship Over “Sink or Swim”: Rather than the traditional approach of pushing new advisors to sell right out of the gate, BFG’s apprenticeship model focuses on gradual learning, client exposure, and holistic development—leading to better advisors and better client outcomes.
4. Excellence Over Perfection: Manny distinguishes himself by expecting perfect effort, not perfect performance, from himself and those around him. He believes in holding high standards while understanding that learning and growth are ongoing processes.
5. Paying It Forward: Manny is committed to giving back—returning to his alma mater, educating others about financial literacy, and striving to be a first-call advocate and steward for his clients and community. He believes true luck and success come at the intersection of preparation and opportunity.

1. Philanthropy Is Personal: Shari emphasized that charitable planning always begins with the client’s unique intent and dreams—never just the technical tools. Professionals must listen deeply to turn intentions into meaningful strategies.
2. Bridging Community Gaps: Recognizing the disconnect between the professional estate planning world and communities of color, Shari founded “Our Legacy Matters” to provide a safe, educational space and bridge miscommunication with accurate, accessible information.
3. Mentorship Matters: A pivotal relationship with her mentor, Aquanetta Betts, shaped Shari’s career and underscored the value of seeking (and becoming) lasting mentors, especially for those without inherited networks or practices.
4. Redefining Generational Philanthropy: Philanthropy in underrepresented communities often centers more on service, time, and talent than on financial gifts—yet these are powerful forms of legacy that deserve recognition and strategic support.
5. The Power of Joyful Reflection: Success isn’t just about relentless achievement. Shari’s decision to pause and intentionally reflect—to “let the sun shine” and dream anew—shows how purposeful rest and pursuit of joy are essential for continued growth.