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
  • Episode 23: Unveiling Amazon FBA Success: From Side Hustles to Serious Money

    Episode 23: Unveiling Amazon FBA Success: From Side Hustles to Serious Money
    Apr 30 2025
    What if you could turn a small product idea into a thriving, automated income stream — and eventually sell it for a life-changing exit? This episode unpacks exactly how to do it. In this episode of Sterling Insights, Roger sits down with Neil Twa, CEO of Voltage Holdings and a leading expert in building and exiting Amazon FBA brands. Together, they explore the world of e-commerce entrepreneurship, sharing valuable insights and practical tips for listeners. Neil draws from his extensive experience — over $100M in online sales and 1,000+ brand launches — to discuss how professionals can transition from the corporate grind to profitable brand owners, offering actionable advice for aspiring entrepreneurs and financial advisors supporting clients on that journey. This episode is a must-listen for anyone exploring new income streams, business ownership, or alternative asset strategies, providing both knowledge and tools to navigate this high-potential space. Key Takeaways: ● 🔍 Amazon as an Opportunity Channel: Amazon isn’t just a marketplace — it’s a logistics machine and data-driven engine that can create scalable income. ● 🧠 From Employee to Operator: Why Neil believes training operators instead of hiring employees is the future of sustainable, exitable businesses. ● 💰 Start with Demand, Not Ideas: Product success doesn’t start with invention — it starts with data. Neil explains how his "Greenlight" tool identifies winning products. ● 🛠 Build for Exit from Day One: Learn how to design a business that not only cash flows, but is also attractive to private equity buyers down the road. ● 🔁 Profit-Driven Priorities: “Revenue is vanity. Profit is sanity.” Neil emphasizes why knowing your numbers and cash flow is key to long-term success. Quotes from Neil Twa: ● “We don’t marry our products — we marry the data that leads us to demand.” ● “Cash flow is king, revenue is vanity, and profit is sanity.” ● “If you're not prioritizing your time, you're choosing to stay stuck — change starts with where you place your energy.” 🔗 Conclusion: If you're looking to build a real, scalable business — or help your clients do the same — this episode delivers the strategy, mindset, and blueprint to make it happen. Connect with Neil at voltagedm.com and explore his book Almost Automated Income to dive deeper into the model. Learn more about your ad choices. Visit megaphone.fm/adchoices
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    32 mins
  • Episode 22: The Art of Buying and Selling Businesses: Strategies for Success

    Episode 22: The Art of Buying and Selling Businesses: Strategies for Success
    Apr 23 2025
    The Art of Buying and Selling Businesses: Strategies for Success Welcome to Episode 22 of Sterling Insights: Sterling Insights: Stand Out & Supercharge Your Assets, hosted by Roger Silk. In this episode, Roger sits down with Richard Parker and discusses Richard’s successful program on buying and selling businesses. Richard Parker has spent over 30 years helping people turn their dream of business ownership into reality. His renowned program, How To Buy A Good Business At A Great Price, has sold over 100,000 copies across more than 80 countries. Richard was also a partner with Ray Dalio and the Dalio family office for four years, where he led an investment firm specifically designed for him to mentor one of Ray’s sons in the art of acquiring businesses. Over the years, Richard has personally acquired 13 companies—plus a co-investment—with purchase prices ranging from $50,000 to over $200 million. His insights have been featured in Forbes, The New York Times, TheStreet.com, Entrepreneur Magazine, Inc., and more, with over 200 published articles to his name. Here are some highlights from the episode: · Richard stresses the value of early preparation when planning to sell a business—resolving operational issues and streamlining processes in advance. Doing so not only boosts the business's appeal to buyers but also increases the chances of a successful sale. · Richard advises business owners not to drain too much cash from their business but to reinvest in strong marketing and quality talent. Strategic investments like these can significantly boost the business’s value when it’s time to sell. · Richard encourages anyone curious about business ownership to explore the opportunity. He emphasizes that entrepreneurship is within reach for most people and recommends learning what it truly involves before making a decision. Connect with Richard: YouTube: https://www.youtube.com/@richardparkerdiomo Facebook: https://www.facebook.com/RichardParkerDiomo Instagram: https://www.instagram.com/richardparkerdiomo/ Linkedin: https://www.linkedin.com/in/richardparkerdiomo/ Connect with Roger: Website: https://www.sterlingfoundations.com Facebook: https://www.facebook.com/sterlingfoundations/ Twitter: https://x.com/SterlingFndMgt?mx=2 LinkedIn: https://www.linkedin.com/company/sterling-foundation-management-llc/ Learn more about your ad choices. Visit megaphone.fm/adchoices
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    31 mins
  • Episode 21: Franchise Maven: Unveiling Lucrative Opportunities for Aspiring Entrepreneurs

    Episode 21: Franchise Maven: Unveiling Lucrative Opportunities for Aspiring Entrepreneurs
    Apr 16 2025
    Welcome to Episode 21 of Sterling Insights: Sterling Insights: Stand Out & Supercharge Your Assets, hosted by Roger Silk. In this episode, Roger sits down with Gregory Mohr and discusses opportunities in franchising and the benefits of owning a franchise. Gregory Mohr is a Wall Street Journal Best Selling author, entrepreneur, and founder of Franchise Maven. A former engineer turned franchise expert, Gregory has helped over 260 people launch 500+ franchise territories. Through his books and coaching, he empowers others to achieve financial freedom and avoid common pitfalls in business ownership—all with a people-first approach rooted in real-world experience. Here are some highlights from the episode: · Gregory explains why franchising offers a proven business model that appeals to individuals seeking financial success, work-life balance, or a legacy. Potential franchisees should assess their risk tolerance and aspirations to find the right fit. · Gregory discusses the importance of having access to a network of professionals to support in making informed decisions when entering the world of franchising. · Gregory explains franchise capital requirements vary—some need significant net worth and liquidity, while service-based franchises often have lower barriers to entry and may qualify for SBA Express loans. Many can be run semi-absentee, offering added flexibility for owners. Connect with Gregory: Website: https://www.franchisemaven.com/ X: https://x.com/Franchise_Maven LinkedIn: https://www.linkedin.com/in/gregorykmohr/ Instagram: https://www.instagram.com/franchisemaven/ Facebook: https://www.facebook.com/FranchiseMaven YouTube: https://www.youtube.com/@Franchise_Maven Connect with Roger: Website: https://www.sterlingfoundations.com Facebook: https://www.facebook.com/sterlingfoundations/ Twitter: https://x.com/SterlingFndMgt?mx=2 LinkedIn: https://www.linkedin.com/company/sterling-foundation-management-llc/ Learn more about your ad choices. Visit megaphone.fm/adchoices
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    34 mins
  • Episode 20: Mastering E-commerce Fraud Protection

    Episode 20: Mastering E-commerce Fraud Protection
    Apr 9 2025
    Mastering E-commerce Fraud Protection Welcome to Episode 020 of Sterling Insights: Sterling Insights: Stand Out & Supercharge Your Assets, hosted by Roger Silk. In this episode, Roger sits down with Dylan Gaines and discusses the importance of fraud protection in e-commerce. Dylan Gaines is the President and co-founder of International Payments Solutions (IPS), a boutique firm specializing in payment processing. With over two decades of industry experience, he launched IPS in 2005 with Chris Gaines, focusing on innovative solutions for e-commerce, retail, and nonprofit merchants. Beyond IPS, Dylan mentors local entrepreneurs and founded The Entrepreneur Club in Clearwater Beach to foster peer-to-peer support. A recognized leader in the space, Dylan is known for his deep industry knowledge and commitment to empowering businesses. Here are some highlights from the episode: · Dylan champions personalized service in payment processing, stressing the value of hands-on experts who guide businesses through payments, fraud prevention, and chargeback management. · International Payment Solutions focuses on e-commerce businesses, providing expert support to navigate payments, prevent fraud, and optimize digital transactions for better protection and performance. · Dylan’s work with entrepreneur clubs and his nonprofit initiative, Payments for a Cause, reflect his commitment to community and social impact—helping business owners turn success into meaningful support for causes they care about. Connect with Dylan: Website: www.intpaysol.com Connect with Roger: Website: https://www.sterlingfoundations.com Facebook: https://www.facebook.com/sterlingfoundations/ Twitter: https://x.com/SterlingFndMgt?mx=2 LinkedIn: https://www.linkedin.com/company/sterling-foundation-management-llc/ Learn more about your ad choices. Visit megaphone.fm/adchoices
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    45 mins
  • Episode 19: Boosting Conversions: Actionable Marketing Tips from 'Stay Paid'

    Episode 19: Boosting Conversions: Actionable Marketing Tips from 'Stay Paid'
    Apr 2 2025
    Welcome to Episode 19 of Sterling Insights: Sterling Insights: Stand Out & Supercharge Your Assets, hosted by Roger Silk. In this episode, Roger sits down with Luke Acree and discusses effective email marketing strategies. Luke Acree is a leadership expert, lead generation specialist, and referral marketing authority who believes strong relationships drive business success. As president of ReminderMedia, he has led the company to over $300 million in sales and secured its place on the Inc. 5000 list for four consecutive years. He co-hosts Stay Paid, a top-ranked marketing podcast, and has been featured in Entrepreneur, Forbes, Yahoo Finance, and more. A sought-after guest, Luke has appeared on SharkPreneur, Marketing Genius, and Real Estate Rockstars. Here are some highlights from the episode: Luke focuses on turning knowledge into action, using his Stay Paid podcast to inspire clients with insights from successful entrepreneurs, motivating them to implement effective marketing strategies. Luke emphasizes the power of personal values and storytelling in building audience rapport. By integrating the three E’s—Education, Entertainment, and Endearment—into their content, financial advisors can establish expertise, captivate their audience, and strengthen connections. Luke highlights the importance of consistency in podcasting and marketing. He emphasizes that success isn’t just about intelligence or appearance but about the ability to quickly turn ideas into action. Connect with Luke: Website: https://remindermedia.com Podcast: https://remindermedia.com/podcast/ Connect with Roger: Website: https://www.sterlingfoundations.com Facebook: https://www.facebook.com/sterlingfoundations/ Twitter: https://x.com/SterlingFndMgt?mx=2 LinkedIn: https://www.linkedin.com/company/sterling-foundation-management-llc/ Learn more about your ad choices. Visit megaphone.fm/adchoices
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    33 mins