PODCAST · business
Your Pathways To Wealth
by Charlie Massimo and Peter Anastasian
Welcome to Your Pathways To Wealth, where Charlie Massimo and Peter Anastasian are on a mission to bring clarity to the world of finances. Together they bring a wealth of knowledge along with years of experience to help you uncover a way to simplify your financial life and help you preserve what you've built and enjoy what you've earned. Join Charlie and Peter, and their guest experts, as they venture to help you continue to grow your wealth..
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24
Why Confidence Doesn’t Come From Beating the Market
As the year comes to a close, many investors look at their statements and feel conflicted. On paper, it may have been a strong year — portfolios held up, markets performed well — yet something still feels unsettled.In this episode of Your Pathways to Wealth, Charlie Massimo and Peter Anastasian unpack why market performance alone rarely delivers lasting confidence, and why so many people feel uneasy even after “good” years.The conversation shifts the focus away from chasing returns and toward what truly builds financial confidence: clarity, coordination, and control — especially around taxes.Charlie and Peter explore how year-end reflection often reveals deeper questions:Can I keep spending like this?What happens if markets struggle at the wrong time?Why does it feel like I’m doing well, but not moving forward?They explain how these concerns are often rooted not in investment risk — but in inefficient tax planning, lack of coordination, and unclear income strategy.???? www.YourPathwaysToWealth.com???? 631-777-1030#YourPathwaysToWealth #FinancialConfidence #RetirementReady #TaxSmart #WealthPlanning #FinancialClarity #InvestWithPurpose
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23
Wellness & Wealth for Women: Why Confidence Begins with Caring for Yourself
Welcome back to Your Pathways to Wealth, the podcast where we explore the decisions, values, and behaviors that allow you to define and enjoy wealth on your own terms. Hosts Charlie Massimo and Peter Anastasian dive into a transformative conversation at the intersection of wellness and wealth — and why taking care of yourself physically and emotionally is essential to living a life aligned with your purpose.They are joined by Karen Sullivan, founder of The Wellness Stop, a functional medicine practice helping women restore energy, balance, vitality, and confidence through personalized, root-cause health strategies. Karen shares her own powerful health journey — one that reshaped her life’s mission — and the profound shifts she sees in women when they reconnect with their wellbeing.In this episode, they discuss:Why women often feel dismissed or unsupported in traditional healthcareThe connection between physical energy, emotional clarity, and financial decision-makingHow midlife transitions can trigger burnout or anxiety — and what to do about itThe foundational role of sleep, stress management, and nutritionSmall steps every woman can take to feel more empoweredAnd how caring for yourself becomes the catalyst for caring for your futureThis is a conversation for every woman stepping into leadership in life, career, or finances — and for those who support them.Connect with Karen Sullivan Website: The Wellness Stop Location: Port Jefferson, NY & Virtual Consultations AvailableConnect with Wealth Enhancement YourPathwaysToWealth.com LinkedIn: Charlie Massimo LinkedIn: Peter AnastasianThe opinions voiced in this recording are for general information only and are not intended to provide specific advice or recommendations for any individual. To determine which strategies or investments may be suitable for you, consult the appropriate qualified professional prior to making a decision.Any company names referenced are for educational purposes only and not an indication of trading intent or a solicitation of their products or services.All investing involves risk including loss of principal. No strategy assures success or protects against loss.
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22
DESIGNING A LIFE WITH INTENTION: BUILDING WEALTH, WELLNESS & COMMUNITY
DESIGNING A LIFE WITH INTENTION: BUILDING WEALTH, WELLNESS & COMMUNITY By YourPathwaysToWealth | July 2025What if a magazine could spark connection, inspire action, and reshape your entire life?In this inspiring episode, Charlie Massimo and Peter Anastasian speak with Sarah Stone, founder and CEO of Intentional Living Magazine, a luxury lifestyle publication and movement that’s about far more than beautiful pages. From building a life in a new country to creating an international brand rooted in authenticity, Sarah shares her powerful journey—and how she helps others design their life with purpose, confidence, and clarity.Sarah’s story of resilience, from publishing setbacks to launching high-touch experiential events, is a masterclass in what it means to lead with both heart and strategy. If you're a woman looking to align wealth, wellness, and your own legacy, this conversation is for you.In this episode, you’ll discover:How Intentional Living Magazine grew from a book into a full-blown media and events platformWhy Sarah refuses to put a date on her magazine—and what that means for timeless impactThe power of curated, intentional marketing over traditional media approachesHow she scaled her brand while staying exclusive and connected to her communityStrategies for inspiring the next generation of women to trust their inner voice and take actionA remarkable story of survival and strength from a Boston Marathon bombing survivor that deeply moved SarahWhy serendipity, shared values, and immersive experiences are key to building relationships—and wealth“Everything we need is within us. We just need to pull it out with the right community, the right inspiration, and the right sphere of influence.” — Sarah StoneLearn More???? IntentionalLivingMagazine.com???? Instagram: @intentionallivingmagazineConnect with Charlie & Peter???? YourPathwaysToWealth.com???? 631-777-1030Pass this episode along to the women in your life—daughters, granddaughters, nieces—who are ready to live with more purpose, power, and possibility.
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21
MASTERING MINDSET: BUILDING CONFIDENCE, RESILIENCE & FINANCIAL AWARENESS
MASTERING MINDSET: BUILDING CONFIDENCE, RESILIENCE & FINANCIAL AWARENESS By YourPathwaysToWealth | July 2025Wealth isn’t just measured in dollars—it’s shaped by mindset.In this energizing episode, Charlie Massimo and Peter Anastasian sit down with Joe LaPietra, founder of Mastery of the Mind, a dynamic program designed to teach mindset, emotional intelligence, and communication skills to students and professionals alike. Joe, a former managing partner in finance and now a passionate speaker and mentor, shares his journey and explains how mental clarity, preparation, and confidence can transform lives—starting as early as ninth grade.You’ll discover how the same principles that shape great athletes and business leaders—like resilience, self-awareness, and the ability to handle rejection—are just as crucial in navigating your financial and personal life.In this episode, you’ll learn:The four “S” stages of success: survival, stability, success, and significanceHow to help kids (and adults) shift from self-doubt to self-beliefThe role of mindset in public speaking, job interviews, and financial decisionsWhy preparation and role-play build lasting confidenceWhat schools and companies get wrong—and how mindset training can close the gapHow to teach financial literacy by connecting behavior to long-term impactWhy rejection is a tool, not a setback—and how to reframe it for growthJoe’s real-world strategies are used by students, athletes, professionals, and financial firms nationwide—and his insight into building the next generation of leaders makes this a can’t-miss episode.“Recognize rejection. Don’t personalize it.” – Joe LaPietraConnect with Joe LaPietra and Mastery of the Mind:???? motmusa.org???? [email protected] with Charlie & Peter:???? YourPathwaysToWealth.com???? 631-777-1030
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20
Think Like a CEO: Treating Your Investments as a Family Business
Think Like a CEO: Treating Your Investments as a Family BusinessBy YourPathwaysToWealth | June 2025 What if you ran your wealth like a $10 million business? In this episode, Charlie Massimo and Peter Anastasian break down themindset shift that high-net-worth individuals need to adopt: treatingtheir portfolio like a business and themselves as the CEO. Fromassembling a trusted team of financial experts to planning forsuccession and unexpected life events, they share why delegation,structure, and discipline are key to sustainable, long-term wealth. Drawing comparisons to the Buss family’s $67 million Lakers investmentand its $10 billion return, Charlie and Peter emphasize how having theright strategy—and support—makes all the difference. They discuss: Why every investor with $5M+ should think like a business owner How hiring a personal CFO team accelerates growth The true cost of doing ityourself (and how it limits your potential) Succession planning andteaching the next generation The importance of perspective, delegation,and adaptability in your financial strategy Avoiding the inefficienciesof managing multiple advisors doing the same thing If you want to shiftfrom managing wealth alone to building something sustainable andscalable with trusted experts, this episode is for you. Connect with Wealth Enhancement: ???? 1-800-492-1222 ????YourPathwaysToWealth.com ???? LinkedIn: Charlie Massimo \| Peter Anastasian
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19
Fixed Income, Market Efficiency, and How to Think About Bonds
In this episode, Charlie and Peter are joined by Doug Longo, afixed-income strategist at Dimensional Fund Advisors, to explore thecomplex world of bonds in a time of uncertainty and market noise. Fromthe yield curve and treasury auctions to how global markets react to newinformation, Doug offers a clear, academic, and data-driven lens on howfixed income works—and why it matters now more than ever. Doug explainswhy bond funds vs. individual bonds are often misunderstood, how marketefficiency plays out differently in stocks and bonds, and why headlinevolatility (like tariffs or treasury concerns) doesn\'t necessarilysignal trouble. With over $120 billion in fixed-income assets,Dimensional uses decades of empirical data—not crystal balls—to navigateglobal bond markets and help investors sleep at night. Whether you\'re aconservative investor or navigating retirement, this episode offerstimeless advice on using fixed income to balance risk, provideliquidity, and support your long-term plan.Find Doug- https://www.linkedin.com/in/douglongouclaanderson/YourPathwaysToWealth.com
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18
Special Needs Planning: Building a Future with Intention
Special Needs Planning: Building a Future with Intention YourPathwaysToWealth | July 2025Planning for a loved one with special needs is a deeply personal and often overwhelming journey, but you don't have to do it alone.In this heartfelt episode, Charlie Massimo and Peter Anastasian sit down with Kelly Piacenti, Head of the Special Care Program at MassMutual and a national authority in special needs planning. Kelly shares her own powerful story as a parent and professional, and explains how families can begin preparing today to ensure a safe, supported, and meaningful future for their loved ones.Connect with the Special Care Program???? Visit MassMutual.com and search for "Special Care" to connect with Kelly and her team.Connect with Charlie & Peter???? YourPathwaysToWealth.com
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17
When Markets Go Down – How to Stay Invested Without Fear
In this episode of Your Pathways to Wealth, Charles Massimo and Peter Anastasian discuss market downturns, the psychology of investing, and how to manage your portfolio through volatility. They emphasize the importance of long-term planning, risk tolerance, and emotional discipline when facing financial uncertainty.Market cycles are inevitable, but how you react to them determines your investment success. Do you panic when you see losses? Do you truly understand your risk exposure? Are you making emotion-driven decisions rather than following a strategic plan? Charlie and Peter explain how to build a resilient portfolio that aligns with your goals so short-term market fluctuations don't derail your long-term financial future.Key Takeaways:✅ Market downturns are normal – They've happened before and will happen again, but history shows recovery follows.✅ Your mindset matters – Staying invested and avoiding emotional decisions can prevent costly mistakes.✅ Diversification is key – Spreading investments across asset classes (stocks, bonds, cash) helps reduce risk.✅ Have a financial plan – If your plan is solid, market declines shouldn't change your strategy.✅ Temporary vs. Permanent Losses – Losses only become real if you sell. Staying invested gives you time to recover.✅ Patience is rewarded – Wealth is built over decades, not overnight. Short-term setbacks don't define long-term success.✅ Don't compare yourself to others – Your financial goals should be based on your needs, not what your neighbors are doing.Charlie and Peter also introduce the Bucket Approach, a smart way to segment investments for different time horizons to ensure you have liquidity, stability, and long-term growth potential.???? Listen now and take control of your financial future!???? Connect with Us:Visit YourPathwaysToWealth.com or call 631-777-1030 for personalized financial guidance.
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16
Understanding Medicare in 2025
Understanding Medicare in 2025 In this episode of Your Pathways toWealth, host Charles Massimo and Peter Anastasian dive into the complexworld of Medicare with expert guest Kevin Lawrence, Director of SeniorMarkets at PGP Benefits. If you\'ve ever felt overwhelmed by Medicareoptions, this episode is for you! Kevin breaks down Medicare Parts A, B,C, and D, the impact of Income-Related Monthly Adjustment Amounts(IRMAA), and the often-overlooked pitfalls of Medicare Advantage vs.Medigap (Supplement) plans. They also discuss the financial consequencesof late enrollment penalties, how retirees living abroad should approachMedicare and strategies for managing Medicare costs through properretirement planning. -Medicare Part A & B: The foundation ofMedicare, covering hospital stays and medical services. -MedicareAdvantage (Part C) vs. Medigap: Pros and cons of each and how to choosethe best plan. -Understanding IRMAA: How your income affects Medicarepremiums and cost reduction strategies. -Late Enrollment Penalties:Avoid lifelong penalties by enrolling at the right time. -Living Abroad& Medicare: What to do if you retire outside the U.S. -Medicare& Special Needs Planning: How SSDI impacts eligibility for thosewith disabilities. -Avoiding Medicare Scams & Misinformation: Commonpitfalls when enrolling. ???? Listen now and take control of your Medicareplanning! ???? Connect with Us: Visit it\'sPathwaysToWealth.com or call631-77Don\'t0 for more information. ???? Special Guest: Kevin Lawrence, PGPBenefits ???? Contact Kevin: [email protected]
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15
Understanding Bonds: Simplifying One of the Most Misunderstood Investments
In this episode of Your Pathways to Wealth, host Charles Massimo and Peter Anastasian tackle one of the most complex and misunderstood aspects of investing: bonds. They discuss why bonds play a vital role in portfolio diversification and risk management, the differences between short-term and long-term bonds, and why staying short-term is a cornerstone of their philosophy.Charlie and Peter break down crucial bond concepts like yield to maturity, duration, and the risks of chasing high yields. They also explore the differences between individual bonds and bond funds, emphasizing the importance of liquidity and understanding what you own. Whether you're a seasoned investor or new to the world of bonds, this episode will provide actionable insights to help you make informed decisions about your fixed-income investments.Takeaways:The Role of Bonds: Bonds help mute portfolio volatility and manage risk, counterbalancing equities.Short-Term vs. Long-Term: Short-term bonds minimize risk and maintain liquidity, protecting investors from market volatility.Yield to Maturity & Duration: Understanding these metrics is key to evaluating bond investments.Risks of Chasing Yield: High-yield bonds often have higher risks, such as leverage or poor credit quality.Transparency in Bond Pricing: Unlike stocks, bonds often lack pricing transparency, so investors must do due diligence.Individual Bonds vs. Bond Funds: Each has advantages; individual bonds provide predictability, while bond funds offer diversification.Keep It Simple: Stick to investments aligned with your risk tolerance and long-term goals.Connect with Us:Visit YourPathwaysToWealth.com or call 631-777-1030 to learn more.This information is not intended as a recommendation. The opinions are subject to change at any time and no forecasts can be guaranteed. Investment decisions should always be made based on an investor's specific circumstances. Investing involves risk, including possible loss of principal.
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14
Preparing for the 2030 Economic Depression
Hosts Charles Massimo and Peter Anastasian share insights, strategies, and expert guest interviews to help listeners navigate financial challenges and opportunities. In this episode, they address the critical factors contributing to the projected 2030 depression based on insights from ITR Economics. Topics include aging demographics, rising healthcare costs, unsustainable entitlement programs, persistent inflation, and mounting national debt. Charlie and Peter discuss how these trends might reshape the economy and what individuals and families can do to prepare. They emphasize the importance of strategic financial planning, risk management, and maintaining liquidity to capitalize on future opportunities. The episode also highlights the significance of making informed investment decisions, social security timing, and real estate in an unpredictable economic landscape. Takeaways: The aging population and labor shortages will reshape global economies. Healthcare costs are rising due to increased demand and stretched resources. Social security and entitlement programs face significant funding challenges. Inflation is likely to remain stubborn, influencing everyday costs and long-term investments. National debt levels may lead to higher taxes and require strategic financial planning. Preparing for economic downturns through diversification, liquidity, and proactive adjustments is key to long-term success. Staying informed and adapting to changing conditions can turn challenges into opportunities for building generational wealth. Connect with Charlie and Peter to explore how their expertise can help you navigate your path to wealth, even in uncertain times. For more information, visit YourPathwaysToWealth.com or call 631-777-1030. Charles Massimo-https://www.linkedin.com/in/charlesmassimo/ Peter Anastasian-https://www.linkedin.com/in/peteranastasian/Disclosures: This information is not intended as a recommendation. The opinions are subject to change at any time and no forecasts can be guaranteed. Investment decisions should always be made based on an investor's specific circumstances. Investing involves risk, including possible loss of principal.
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13
The Current State of Medicine with Dr. Dicapua
Today, we're diving deep into the current state of medicine and the unique financial challenges and opportunities facing physicians.Joining us is our very special guest and client, doctor John DiCapua, a prominent figure in the field of anesthesiology and the former CEO of North American Partners in Anesthesia, or NAPA that some may know it by, one of the largest anesthesia management companies in the US, known for its innovative approach to patient care and clinician support.
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12
Allison Kleinman and Alex LoPinto: Future Centered Care
Allison Kleinman and Alex LoPinto from Future Centered Care discuss their work in supporting individuals with developmental disabilities and their families. They share their personal journeys and how they came to create Future Centered. The conversation covers topics such as employment, housing, and overseeing care as adults age. They emphasize the importance of creating future options and overseeing care for individuals with disabilities. They also discuss the challenges of finding suitable housing and managing expectations. The conversation highlights the need for personalized and tailored support for each family and individual. Future Centered aims to provide housing solutions and support for adults with intellectual and developmental disabilities. They focus on creating individualized programs and promoting inclusivity. They offer various models, such as live-in caregivers and clustered housing, to address the housing needs of this population. Future Centered also works on advocating for set-aside housing and educating developers on the incentives available. They emphasize the importance of sustainability and building a strong support network. The organization aims to expand its footprint beyond New York City and provide resources to families across the country. Takeaways: Future Centered Care provides support for individuals with developmental disabilities and their families, focusing on employment, housing, and overseeing care as adults age. They work closely with families to create personalized plans and goals, addressing immediate, intermediate, and long-term needs. Managing expectations is crucial, and they emphasize the importance of open communication and regular updates. Finding suitable housing is a significant challenge, and they explore various options and resources available to families. Collaboration with wealth managers and financial planning is essential to ensure adequate funding for future needs. They promote inclusivity and individualized programs to meet the unique needs of each individual. Future Centered Care advocates for set-aside housing and educates developers on incentives. Building a strong support network and ensuring sustainability are key goals for Future Centered Care. Connect with Wealth Enhancement Group: 1-631-777-1030 Wealth Enhancement Group LinkedIn: Charlie Massimo LinkedIn: Peter Anastasian Disclosures The opinions voiced in this recording are for general information only and are not intended to provide specific advice or recommendations for an individual. To determine which strategies or investments may be suitable for you, consult the appropriate qualified professional prior to making a decision. Any company names noted herein are for educational purposes only and not an indication of trading intent or a solicitation of their products or services. All performance referenced is historical and is no guarantee of future results. All indices are unmanaged and may not be invested into directly. All investing involves risk including loss of principal. No strategy assures success or protects against loss. There is no guarantee that a diversified portfolio will enhance overall returns or outperform a non-diversified portfolio. Diversification does not protect against market risk.See omnystudio.com/listener for privacy information.
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11
Becky Fawcett: Building and Growing Help Us Adopt
Becky Fawcett, founder of Help Us Adopt, shares her journey of starting a nonprofit organization that provides financial assistance to families to help with the cost of adoption. She discusses the challenges she faced in her own adoption journey and how it inspired her to help others. Becky highlights the importance of family equality and the need for larger adoption grants to truly solve the financial barriers. She also talks about the changing landscape of adoption, including the impact of social media and the effects of COVID-19 and war on international adoptions. Becky emphasizes the significance of open adoptions and the positive experiences she has had with birth parents. She concludes by discussing the growth of Help Us Adopt. Becky Fawcett discusses how she built an amazing board for HelpUsAdopt.org and the importance of running a nonprofit like a business. She emphasizes the need for fiscal responsibility and making decisions that align with the organization's mission. Becky shares her strong-willed and aggressive approach to building the organization and not being afraid to make tough decisions. She also talks about the importance of knowing the difference between 'no' and 'not yet' and the power of perseverance. Takeaways The cost of adoption is a significant obstacle for many families, and organizations like Help Us Adopt provide crucial financial assistance. Family equality is an important aspect of adoption, and it is essential to support all types of families. The landscape of adoption has changed with the rise of social media and the impact of COVID-19 and war on international adoptions. Open adoptions can be a positive experience for all parties involved and can create lifelong connections. Help Us Adopt has grown from a small organization to a national one with a focus on providing larger grants to solve the financial barriers of adoption. Building a strong board is crucial for the success of a nonprofit organization. Running a nonprofit like a business, with fiscal responsibility and strategic decision-making, is essential for long-term growth. Knowing the difference between 'no' and 'not yet' can help navigate challenges and setbacks. Finding your purpose doesn't necessarily mean starting a nonprofit; it can be about making a difference in any area that you care about. Recommended books: 'The Authenticity Project' by Clare Pooley and 'American Baby' by Gabrielle Glaser. Connect with Wealth Enhancement Group: 1-631-777-1030 Wealth Enhancement Group LinkedIn: Charlie Massimo LinkedIn: Peter Anastasian Disclosures The opinions voiced in this recording are for general information only and are not intended to provide specific advice or recommendations for an individual. To determine which strategies or investments may be suitable for you, consult the appropriate qualified professional prior to making a decision. Any company names noted herein are for educational purposes only and not an indication of trading intent or a solicitation of their products or services. All performance referenced is historical and is no guarantee of future results. All indices are unmanaged and may not be invested into directly. All investing involves risk including loss of principal. No strategy assures success or protects against loss. There is no guarantee that a diversified portfolio will enhance overall returns or outperform a non-diversified portfolio. Diversification does not protect against market risk.See omnystudio.com/listener for privacy information.
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10
Laurie Spampinato: Balance and Preparing for the Unexpected
Laurie Spampinato shares her experience of rebuilding her life and managing her finances after the tragedy of 9/11 with hosts Charlie Massimo and Peter Anastasian. She discusses the importance of being financially prepared and having a plan in place, as well as the role of women in managing wealth. Laurie emphasizes the need for open communication and involvement in financial matters, regardless of gender. She also highlights the importance of prioritizing goals and making smart financial decisions to ensure a stable future. In this conversation, Laurie discusses the importance of trusted support and the need for women to be involved in financial planning. She shares her experience of losing her husband and the challenges she faced as a widow. Laurie emphasizes the value of having a trusted advisor and the importance of preparing for the unexpected. She also talks about her changing priorities as her children have grown up and the need to balance saving for the future with enjoying the present. Takeaways Be financially prepared and have a plan in place for unexpected events. Open communication and involvement in financial matters are crucial. Prioritize goals and make smart financial decisions for a stable future. Trusted support is crucial for individuals who have lost a spouse unexpectedly. Having a trusted advisor, such as a fiduciary, can provide guidance and help make informed financial decisions. Everyone should be actively involved in financial planning and have open conversations with their partners about their financial goals and priorities. Preparing for the unexpected, such as the loss of a spouse or divorce, is essential for financial security. Balancing saving for the future with enjoying the present is a challenge that many individuals face. Connect with Wealth Enhancement Group: 1-631-777-1030 Wealth Enhancement Group LinkedIn: Charlie Massimo LinkedIn: Peter Anastasian Disclosures The opinions voiced in this recording are for general information only and are not intended to provide specific advice or recommendations for an individual. To determine which strategies or investments may be suitable for you, consult the appropriate qualified professional prior to making a decision. Any company names noted herein are for educational purposes only and not an indication of trading intent or a solicitation of their products or services. All performance referenced is historical and is no guarantee of future results. All indices are unmanaged and may not be invested into directly. All investing involves risk including loss of principal. No strategy assures success or protects against loss. There is no guarantee that a diversified portfolio will enhance overall returns or outperform a non-diversified portfolio. Diversification does not protect against market risk.See omnystudio.com/listener for privacy information.
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ABOUT THIS SHOW
Welcome to Your Pathways To Wealth, where Charlie Massimo and Peter Anastasian are on a mission to bring clarity to the world of finances. Together they bring a wealth of knowledge along with years of experience to help you uncover a way to simplify your financial life and help you preserve what you've built and enjoy what you've earned. Join Charlie and Peter, and their guest experts, as they venture to help you continue to grow your wealth..
HOSTED BY
Charlie Massimo and Peter Anastasian
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