Watch Your Six

Jason Edwards
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  • UPDATED WEEKLY

As a financial advisor with nearly two decades of experience, I've seen firsthand that the biggest challenge for my clients—whether business leaders, entrepreneurs, or individuals looking to grow their wealth—is the fixation on picking the "right" investments. In reality, success lies in avoiding the wrong ones. The goal isn't to beat the market; it's to follow a disciplined, strategic plan that allows your wealth to grow steadily over time. My passion has always been to protect and guide my clients toward smart financial decisions, and I want to do the same for you. Each week on our show, we'll speak with people who have been misled, made costly mistakes, or fallen victim to bad financial advice. We'll break down their experiences and provide insights to help you avoid the same pitfalls—so you can build and protect your wealth with confidence.

  1. 1D AGO

    Good Debt vs. Bad Debt | #37

    Most people aren't broke because they don't make money. They're broke because nobody taught them how to use it. In this episode of Watch Your Six, host Jason Edwards breaks down one of the biggest financial misconceptions out there: the difference between good debt and bad debt. From credit cards and cash flow mistakes to real estate strategy, liquidity, and alternative investments, Jason explains how wealthy investors think differently about money and why having a plan matters more than chasing trends. He also dives into how entrepreneurs and young investors can avoid getting cash poor, why being "debt free" isn't always the smartest move, and the investment strategies many traditional advisors never talk about. Key takeaways: Why liquidity can be more valuable than owning assets outright The difference between emotional decisions and strategic investing How alternative investments are used by high-net-worth investors Simple habits that can change your financial future If you want to build wealth with intention instead of emotion, this episode is for you.   🎙️ Watch Your Six — helping you safeguard your financial future. 📌 Connect with Jason Edwards: LinkedIn | Email | Watch Your Six 🎙️ Follow the show: Watch Your Six Securities offered through Calton & Associates, Inc. member FINRA and SIPC, a Registered Investment Adviser Investment advisory services offered through Edwards Financial Services, Inc., a Registered Investment Adviser Edwards Financial Services, Inc. is not owned or controlled by Calton & Associates, Inc.   The information contained in this communication has been derived from sources believed to be reliable but is not guaranteed as to the accuracy and completeness and does not purport to be a complete analysis of the material discussed. The opinions expressed herein do not necessarily reflect those of Calton and Associates, Inc., and are subject to change without notice.

    25 min

  2. APR 29

    How Smart Investors Stay Calm | #36

    When markets get noisy, the smartest move is often staying steady. In this episode of From Underdog to Entrepreneur, host Pat Miller breaks down what rising oil prices, market pullbacks, and shifting consumer trends really mean for your money. He shares why panic can be costly, how disciplined investors use downturns as opportunity, and why understanding the next generation of buyers could shape future wealth. You'll also hear why many high earners still struggle financially, how to choose the right financial team, and what separates investing from gambling. Key Takeaways: • Why market dips can create buying opportunities • How Gen Alpha is already influencing spending habits • Why income alone does not equal wealth Success favors the prepared, not the panicked. Tune in and build smarter from here.

    25 min

  3. APR 21

    Stop Waiting, Start Investing Smart | #35

    What if the biggest risk in today's market is doing nothing at all? In this episode of Watch Your Six, Jason Edwards breaks down why fear-driven investing can cost you more than market volatility. With global uncertainty, rising costs, and constant headlines, he explains how smart investors find opportunity where others hesitate and why timing the market is a losing game. You'll learn how to think strategically about your money, avoid common pitfalls, and recognize where growth is actually happening even when the news says otherwise. Key takeaways: Why avoiding bad decisions matters more than chasing big wins How market trends and simple indicators can reveal hidden opportunities Where real growth can exist during economic uncertainty If you've been sitting on the sidelines waiting for the "perfect time," this episode will challenge you to rethink everything and take control of your financial future.

    26 min

  4. MAR 31

    Oil, Panic, and Costly Money Mistakes | #34

    Gas prices are rising—but not for the reasons you think. Jason Edwards breaks down the real forces behind oil price spikes, why media-driven panic can cost you money, and how smart investors actually respond during market corrections. He also uncovers a surprising economic driver most people overlook: Gen Alpha—and how their behavior is shaping the future of spending, business, and investing. From avoiding emotional decisions to building a real financial strategy, this episode is a practical guide to staying ahead when markets get noisy.   🎙️ Watch Your Six — helping you safeguard your financial future. 📌 Connect with Jason Edwards: LinkedIn | Email | Watch Your Six 🎙️ Follow the show: Watch Your Six Securities offered through Calton & Associates, Inc. member FINRA and SIPC, a Registered Investment Adviser Investment advisory services offered through Edwards Financial Services, Inc., a Registered Investment Adviser Edwards Financial Services, Inc. is not owned or controlled by Calton & Associates, Inc.   The information contained in this communication has been derived from sources believed to be reliable but is not guaranteed as to the accuracy and completeness and does not purport to be a complete analysis of the material discussed. The opinions expressed herein do not necessarily reflect those of Calton and Associates, Inc., and are subject to change without notice.

    23 min

  5. MAR 24

    When Markets Drop, Lean In | #33

    When global conflict shakes the markets, most people panic. The smartest investors do the opposite. In this episode of Watch Your Six, host Jason Edwards breaks down how geopolitical conflict, oil markets, and economic uncertainty can impact your portfolio. More importantly, he explains why market corrections may actually be one of the biggest opportunities investors ever get. Instead of reacting emotionally, Jason shares how strategic thinking, strong fundamentals, and the right team can turn volatility into long term growth. You will learn why market pullbacks often create powerful investment opportunities and how disciplined investors position themselves ahead of the rebound. Key insights in this episode: Why market corrections can be opportunities instead of threats How geopolitical conflict affects oil, trade, and global markets The power of dollar cost averaging during volatile times When others panic, opportunity quietly appears. Tune in to learn how disciplined investors stay focused, think long term, and position themselves to win when the market recovers. 🎙️ Watch Your Six — helping you safeguard your financial future. 📌 Connect with Jason Edwards: LinkedIn | Email | Watch Your Six 🎙️ Follow the show: Watch Your Six Securities offered through Calton & Associates, Inc. member FINRA and SIPC, a Registered Investment Adviser Investment advisory services offered through Edwards Financial Services, Inc., a Registered Investment Adviser Edwards Financial Services, Inc. is not owned or controlled by Calton & Associates, Inc.   The information contained in this communication has been derived from sources believed to be reliable but is not guaranteed as to the accuracy and completeness and does not purport to be a complete analysis of the material discussed. The opinions expressed herein do not necessarily reflect those of Calton and Associates, Inc., and are subject to change without notice.

    16 min

  6. MAR 17

    The Truth About Market Pullbacks | #32

    When the market dips, most investors panic. But what if that pullback is actually your biggest opportunity?   In this episode of Watch Your Six, host Jason Edwards breaks down what really drives market corrections and why emotional investing can cost you in the long run. From the explosive growth of AI infrastructure to overlooked sectors like data storage and energy, Jason explains how disciplined strategy and long term thinking can help investors stay ahead of the curve.   In this episode you will hear about: Why market pullbacks may be opportunities, not disasters The hidden industries fueling the AI boom How diversification protects your portfolio when markets get volatile   If you want a clearer perspective on today's markets and where opportunity may be hiding, this conversation will help you think differently about investing. 🎙️ Watch Your Six — helping you safeguard your financial future. 📌 Connect with Jason Edwards: LinkedIn | Email | Watch Your Six 🎙️ Follow the show: Watch Your Six Securities offered through Calton & Associates, Inc. member FINRA and SIPC, a Registered Investment Adviser Investment advisory services offered through Edwards Financial Services, Inc., a Registered Investment Adviser Edwards Financial Services, Inc. is not owned or controlled by Calton & Associates, Inc.   The information contained in this communication has been derived from sources believed to be reliable but is not guaranteed as to the accuracy and completeness and does not purport to be a complete analysis of the material discussed. The opinions expressed herein do not necessarily reflect those of Calton and Associates, Inc., and are subject to change without notice.

    23 min

  7. MAR 10

    Why Most Small Businesses Fail | #31

    Most businesses do not fail because of bad ideas. They fail because they run out of cash. In this episode of Watch Your Six, host Jason Edwards sits down with Tim, founder of Tim's Wine Market in Orlando, to break down what it really takes to survive and thrive for 30 years in a competitive industry. From jumping into entrepreneurship at 27 to navigating big box competition, shifting consumer trends, and economic downturns, Tim shares the hard truths most aspiring business owners never hear. This is not theory. It is three decades of real world lessons. In this episode, you will learn: Why undercapitalization quietly kills great businesses How to find your niche instead of competing with giants Why a business plan and pro forma are non negotiable How to pivot, evolve, and survive industry cycles If you are thinking about starting a business, already running one, or trying to scale without burning out, this conversation will challenge the way you think about risk, growth, and cash flow. Success is not about having the best idea. It is about having the discipline to build it right.   🎙️ Watch Your Six — helping you safeguard your financial future. 📌 Connect with Jason Edwards: LinkedIn | Email | Watch Your Six 🎙️ Follow the show: Watch Your Six Securities offered through Calton & Associates, Inc. member FINRA and SIPC, a Registered Investment Adviser Investment advisory services offered through Edwards Financial Services, Inc., a Registered Investment Adviser Edwards Financial Services, Inc. is not owned or controlled by Calton & Associates, Inc.   The information contained in this communication has been derived from sources believed to be reliable but is not guaranteed as to the accuracy and completeness and does not purport to be a complete analysis of the material discussed. The opinions expressed herein do not necessarily reflect those of Calton and Associates, Inc., and are subject to change without notice.

    27 min

  8. JAN 27

    Why 2026 Could Make Millionaires | #30

    The noise is loud, the fear is high—but the facts tell a very different story about what's coming next.  In this episode of Watch Your Six, Jason Edwards cuts through the headlines to explain why 2026 is shaping up to be a uniquely powerful year for investors. From falling inflation and potential rate cuts to AI-driven efficiency and global market opportunities, Jason breaks down how today's economic tailwinds could translate directly into real wealth-building opportunities for everyday investors. Rather than chasing hype or freezing in uncertainty, this conversation focuses on building a disciplined strategy that positions you to benefit from one of the most robust bull environments in years.   Key themes discussed: Why removing fear and focusing on facts changes everything How AI, energy, healthcare, and consumer sectors are quietly compounding growth The danger of "paralysis by analysis" and why waiting can cost you the most   2026 isn't about guessing—it's about preparation. Get positioned, get informed, and get ready to move with confidence.   🎙️ Watch Your Six — helping you safeguard your financial future. 📌 Connect with Jason Edwards: LinkedIn | Email | Watch Your Six 🎙️ Follow the show: Watch Your Six Securities offered through Calton & Associates, Inc. member FINRA and SIPC, a Registered Investment Adviser Investment advisory services offered through Edwards Financial Services, Inc., a Registered Investment Adviser Edwards Financial Services, Inc. is not owned or controlled by Calton & Associates, Inc.   The information contained in this communication has been derived from sources believed to be reliable but is not guaranteed as to the accuracy and completeness and does not purport to be a complete analysis of the material discussed. The opinions expressed herein do not necessarily reflect those of Calton and Associates, Inc., and are subject to change without notice.

    14 min
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About

As a financial advisor with nearly two decades of experience, I've seen firsthand that the biggest challenge for my clients—whether business leaders, entrepreneurs, or individuals looking to grow their wealth—is the fixation on picking the "right" investments. In reality, success lies in avoiding the wrong ones. The goal isn't to beat the market; it's to follow a disciplined, strategic plan that allows your wealth to grow steadily over time. My passion has always been to protect and guide my clients toward smart financial decisions, and I want to do the same for you. Each week on our show, we'll speak with people who have been misled, made costly mistakes, or fallen victim to bad financial advice. We'll break down their experiences and provide insights to help you avoid the same pitfalls—so you can build and protect your wealth with confidence.

Information

  • Creator
    Jason Edwards
  • Years Active
    2025 - 2026
  • Episodes
    37
  • Rating
    Clean
  • Copyright
    © 2025
  • Show Website
    Watch Your Six