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Sterling Insights

Sterling Insights

By: Roger Silk
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 Tune into Sterling Insights: Stand Out & Supercharge Your Assets, the premier podcast for financial advisors in growth mode who serve high net worth clients. If you work with clients who own appreciated capital assets and are looking to sell without incurring capital gains taxes, this show is for you. Each episode features insights and strategies from top financial advisors, experienced lawyers, and knowledgeable CPAs. Learn practical solutions to help your clients maximize their wealth while minimizing taxes, and discover how to grow your assets under management. Join us on Sterling Insights and empower your advisory practice with the knowledge to succeed.Copyright 2024 Sterling Insights. Roger Silk. All Right Reserved. Economics Leadership Management & Leadership Marketing Marketing & Sales Personal Finance
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Episodes
  • Bonus: Navigating the Art of Accounting

    Bonus: Navigating the Art of Accounting
    May 15 2025
    What if cleaning up messy finances could feel as satisfying as creating a work of art? Tune in to hear how one expert turns tax chaos into clarity! In this episode of Sterling Insights, guest host Charles Trakas sits down with Karen Cassidy, Enrolled Agent and Founder of Cassidy Accounting. Together, they explore how small business owners can get a handle on messy books, avoid tax pitfalls, and prepare for financial success, sharing valuable insights and practical tips for listeners. Karen draws from her 41+ years of accounting experience to discuss the real-world challenges of tax compliance, client management, and staying resilient through personal obstacles, offering actionable advice for small business owners, entrepreneurs, and anyone struggling with financial organization. This episode is a must-listen for small business owners, solo entrepreneurs, and professionals wanting to better manage their finances, providing both knowledge and tools to navigate this important subject. Key Takeaways: ● 🧾 The Role of an Enrolled Agent: Understanding the unique authority and advantages EAs have over CPAs for federal tax representation. ● 🏛 Building a Client-Centric Business: Why Karen loves working with small businesses and how she tailors services to their unique needs. ● 💬 Communication is Key: How setting boundaries and expectations upfront helps maintain healthy client relationships. ● 🧹 Fixing Financial Messes: Karen’s passion for helping clients untangle years of backlogged taxes and messy bookkeeping. ● 🧠 Resilience Through Challenges: Karen’s inspiring journey overcoming mental health struggles to earn multiple degrees and rebuild her career Quotes from Karen Cassidy: ● "Sometimes you have to tweak the rules a little bit — because sometimes you have to be human." ● "You can attain your dreams, even if it takes longer and the path isn’t straight." ● "Taking a financial mess and making sense of it — it’s like creating a work of art." 🔗 Conclusion: If you're a small business owner feeling overwhelmed by taxes or bookkeeping, Karen’s story proves it’s never too late to get organized and thrive. Connect with Karen Cassidy: Website: www.cassidyaccounting.com Learn more about your ad choices. Visit megaphone.fm/adchoices
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    26 mins
  • Episode 25: Unveiling the Quantum Leap from Physics to Finance

    Episode 25: Unveiling the Quantum Leap from Physics to Finance
    May 14 2025
    Can a Bond Help You Transfer Millions Tax-Free? In this episode of Sterling Insights, Roger sits down with Edward Condon, founder of Regatta Advisors and creator of Structured GRAT. Together, they explore how structured investments can be used within Grantor Retained Annuity Trusts (GRATs) to efficiently transfer wealth while minimizing gift taxes. Ed draws from his decades of experience in physics, finance, and structured product development to break down the mechanics and strategy behind this high-level planning tool. This episode is a must-listen for estate attorneys, financial advisors, and family offices looking to unlock the full potential of GRATs using custom-built structured note portfolios. 🎯 Key Takeaways: 💼 What Structured Notes Really Are: Structured notes are customized debt instruments that link returns to market indices, giving investors targeted exposure while offering downside protection. 🏛️ Why GRATs Work for the Ultra-Wealthy: GRATs enable the tax-free transfer of asset growth beyond a set hurdle rate—ideal for portfolios exceeding $25M. 🔄 How Custom Notes Enable Liquidity & Scalability: By tailoring notes to match annual GRAT payments, Ed’s team helps diversify credit risk and optimize for capital gains tax treatment. 🧠 Analytics Make or Break GRAT Success: Ed’s proprietary backtesting platform shows how different configurations can produce GRAT success rates above 95%. 🔍 Common Misconceptions Around Structured Products: Structured notes aren’t opaque hedge fund bets—they’re designed, collateralized, and executed for stability and transparency when done correctly. 💬 Quotes from Ed Condon: "Structured notes let you customize the payoff profile to match the specific goals of the GRAT—it's not a one-size-fits-all approach." "I realized you could unlock GRATs for liquid portfolios by designing illiquid-qualifying assets from scratch." "The combination of customization, discountability, and predictable performance makes structured notes uniquely suited for wealth transfer." 🔗 Conclusion: If you work with ultra-high-net-worth families or are one, this episode shows how advanced analytics and tailored financial engineering can maximize legacy planning. Connect with Ed: Website: structuredgrat.com Learn more about your ad choices. Visit megaphone.fm/adchoices
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    44 mins
  • Episode 24: Mastering Creative Real Estate Deals

    Episode 24: Mastering Creative Real Estate Deals
    May 7 2025
    Imagine buying real estate without using banks, large amounts of cash, or putting your personal credit on the line — that's exactly what Chris Prefontaine teaches, and in this episode, he shares the recession-proof strategies behind it. In this episode of Sterling Insights, Roger sits down with Chris Prefontaine, founder of Smart Real Estate Coachand a veteran real estate investor with over 30 years of experience. Together, they explore how to close creative real estate deals without using banks or personal cash, sharing valuable insights and practical tips for listeners. Chris draws from his extensive experience to discuss how creative financing can help investors build wealth while minimizing risk, offering actionable advice for aspiring and seasoned real estate investors. This episode is a must-listen for anyone looking to create financial freedom through real estate without the traditional barriers. Key Takeaways: ● 🏡 Creative Financing Works: Chris breaks down how owner financing, lease purchases, and subject-to deals allow you to buy properties with little to no money or credit. ● 💬 Motivated Sellers Matter: Success hinges on finding sellers with genuine motivation — not every property is a good fit. ● 🛠️ No Landlord Headaches: By using rent-to-own strategies, you can transfer maintenance and repair responsibilities to tenant-buyers. ● 📈 Three-Payday System: Chris explains how his system generates upfront cash, ongoing cash flow, and a backend profit, all without traditional bank loans. ● 🎯 Stay Focused for Success: The biggest factor in succeeding is avoiding "shiny object syndrome" and committing to a strategy for 3–5 years. Quotes from Chris Prefontaine: ● "We don’t use banks. We buy only through owner financing, subject-to existing financing, and lease purchase — none of those require gobs of cash or banks." ● "Motivation is key. Without it, you’re wasting time. We look for sellers who need to move, not just want to." ● "Put the blinders on for three to five years. The ones who stay focused are the ones who build real wealth." 🔗 Conclusion: Chris Prefontaine shows that creative real estate can offer a powerful path to financial freedom — without the traditional barriers of credit, cash, or banks. Connect with Chris: Website: smartrealestatecoach.com/connect Free Book Request: https://wickedsmartbooks.com/rogersilk Master’s Class: www.smartrealestatecoach.com/mastersclass 15-Minute Strategy Call: www.smartrealestatecoach.com/action Learn more about your ad choices. Visit megaphone.fm/adchoices
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    30 mins

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