Sterling Insights

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.

  1. 4D AGO

    Building a $25M+ Minimum Family Office for First-Gen Entrepreneurs

    What does it take to build a family office with a $25M minimum and serve first-generation entrepreneurs navigating complex wealth? This episode breaks it down. In this episode of Sterling Insights, Roger sits down with Chad Willardson, founder of Pacific Capital and advisor to ultra-high-net-worth founders. Together, they explore how to serve first-gen entrepreneurs with complex financial lives, sharing valuable insights and practical tips for advisors and families alike. Chad draws from his extensive experience building a boutique family office to discuss client fit, private investments, multi-generational planning, and how to say no—even to $100M prospects, offering actionable advice for those working with high-net-worth individuals. This episode is a must-listen for financial advisors, family office professionals, and entrepreneurial families, providing both knowledge and tools to navigate this important subject. Key Takeaways: ● 💼 Know Your Ideal Client: Why Chad only serves first-gen founders with $25M+ and how he defines perfect-fit clients. ● 🧠 Be the Peer, Not Just the Planner: How being an entrepreneur himself makes Chad more effective as an advisor. ● 📊 Private Deals Are Everywhere: How his team evaluates hundreds of private investment opportunities each year for clients. ● 🧒 Smart, Not Spoiled: Why teaching kids about money early is essential—and how not to ruin the next generation. ● 🛩️ Lifestyle Decisions Matter: What to consider when clients ask, “Should I buy a jet?” Quotes from Chad Willardson: ● "I’m more of a peer to my clients than just their advisor." ● "You don’t have to do business with people who aren’t a good personal fit." ● "Making money easy doesn’t make someone good with money." 🔗 Conclusion: Serving ultra-wealthy entrepreneurs isn’t just about investing—it’s about simplifying their lives, protecting their time, and helping them think clearly in high-stakes moments. Connect with Chad: Website:  http://chadwillardson.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

    30 min

  2. 5D AGO · BONUS

    Estate Planning for Business Owners: Protect Assets, Cut Taxes, Build Legacy

    You might think you have time to plan your legacy—but waiting too long could cost your family dearly. In this episode of Sterling Insights, host Seth Krussman sits down with Aaron Frishman, of counsel at Gevurtz Menashe and an expert in estate, tax, and elder law planning. Together, they explore the complexities of estate planning for business owners and high-net-worth families, sharing valuable insights and practical tips to protect what matters most. Aaron draws from over two decades of legal experience to discuss common missteps, asset protection strategies, and long-term care planning, offering actionable advice for families, entrepreneurs, and financial professionals alike.This episode is a must-listen for business owners, advisors, and affluent families looking to stay ahead of tax changes, preserve generational wealth, and avoid costly planning mistakes.Key Takeaways: 🧠 Plan Early: Waiting too long to start estate planning often leads to unnecessary taxes, legal confusion, or family conflict. 🏠 Avoid Probate: Use revocable trusts and proper titling to ensure smooth transitions and privacy for heirs. ⚖️ State Taxes Matter: Oregon and Washington have aggressive estate tax thresholds that catch many families off guard. 👨‍👩‍👧 Family Assumptions Are Dangerous: Assigning roles based on tradition (like making the oldest child a trustee) can backfire—fit matters more than form. 🛡️ Long-Term Care Planning Is Crucial: Without insurance or trust-based strategies, healthcare costs can drain family wealth quickly. “Most people think they have more time. The truth is, things change fast—and if you wait, your options shrink.” “A trust with nothing in it is like a safe with no valuables. You have to fund it, or it’s just a document.” “Just because someone’s your oldest child doesn’t mean they’re the right person to manage your estate.” Quotes from Aaron Frishman:🔗 Conclusion: Estate planning isn’t just for the ultra-wealthy—it’s about protecting your legacy, your family, and your future. Starting now is the smartest move you can make.Connect with Aaron:Website:  www.gevurtzmenashe.com LinkedIn:  https://www.linkedin.com/in/aaronfrishman/With Your Guest Host Seth Krussman:Seth Krussman is a seasoned financial advisor and partner at Brayshaw Financial Group, LLC, with over 30 years of experience in entrepreneurship, business development, and wealth management. A Registered Representative and Investment Advisor Representative with Osaic Wealth, Inc., Seth specializes in tax-efficient investment strategies, executive compensation, and succession planning for high-net-worth clients. Based in Hillsboro, Oregon, he is also the nationally recognized co-host of the radio show Money On Tap and an active community leader, husband, and father.Connect with Seth:Website:  https://www.brayshawfinancial.com/Podcast:  https://www.brayshawfinancial.com/money-on-tapFacebook:  https://www.facebook.com/3Dinvesting/X:  https://x.com/BFG_LLC/ Learn more about your ad choices. Visit megaphone.fm/adchoices

    45 min

  3. 12/24/2025

    How Top Advisors Scale with Purpose Using the 80/20 Rule and Practice Management

    Most advisors manage money—but what separates the top 20% from the rest is how they manage relationships, structure their practice, and scale with intention. Are you investing your time where it matters most? In this episode of Sterling Insights, Roger sits down with Duncan MacPherson, CEO of Pareto Systems and a practice management expert for top financial advisors. Together, they explore how elite advisors create enterprise value by professionalizing their client experience, sharing valuable insights and practical tips for listeners. Duncan draws from over 30 years of experience to discuss the pitfalls of plateauing, the power of process, and how to grow a business that truly serves your life. This episode is a must-listen for advisors who work with high-net-worth clients and want to grow by design—not by default, providing both knowledge and tools to navigate this critical evolution. Key Takeaways: ● 🧠 The 80/20 Principle in Practice: How elite advisors focus 80% of their energy on the 20% of clients who drive results—and why most advisors still get it backward. ● 🛠️ Professionalizing the Client Experience: Why it’s no longer enough to rely on product and performance, and how to build a proprietary process that creates real differentiation. ● 📈 From Practice to Business: The stages of growth—growing, teaming, scaling, and exiting—and how to move from reactive to intentional. ● 🎯 Finding and Serving Your Ideal Client: Tools like the Practice Management Index (PMI) help advisors identify gaps and realign around what matters most. ● 🤝 Positioning vs. Pitching: Why complex clients don’t want to be sold—they want to buy into a vision, process, and partnership. Quotes from Duncan MacPherson: ● "You’re not asking a client to buy something—you’re asking them to buy into something." ● "The business is supposed to serve your life, not the other way around." ● "If you're not adapting, you're plateauing. Minor adjustments over time can lead to major improvements." 🔗 Conclusion: Success today isn’t just about assets under management—it’s about building a business with process, purpose, and professional contrast. If you want to scale intentionally and future-proof your practice, this episode is your starting point. Connect with Duncan: Website:  www.paretosystems.com Podcast:  https://always-on-with-d-macpherson.blubrry.net/ 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

    32 min

  4. 12/23/2025 · BONUS

    Succession, Governance & Growth: How CPA Firms Build Transferable Value

    Are CPA firms really ready for succession—or just hoping they’ll figure it out later? Discover why waiting is the costliest mistake a firm can make.In this episode of Sterling Insights, guest host Charles Trakas sits down with a seasoned advisor and CPA-turned-growth consultant, Daniel McMahon. Together, they explore succession planning, governance, and building enterprise value in CPA firms, sharing valuable insights and practical tips for listeners. Drawing from decades of experience in public accounting and management consulting, the guest unpacks the common challenges firms face when planning for transition and offers actionable advice to create firms that are sustainable, transferable, and truly valuable.This episode is a must-listen for firm leaders, partners, and advisors working with CPA firms, providing both knowledge and tools to navigate succession with confidence.Key Takeaways:● 🔁 Succession Is a Process, Not an Event: Planning early and treating succession like a process—rather than a one-time event—ensures smoother transitions and sustained firm value.● 🧱 Strong Governance Builds Strong Firms: Implementing clear governance structures creates accountability, alignment, and sets the foundation for long-term growth.● 🕰️ The Tyranny of the Now: Many firm owners delay planning because they’re overwhelmed by day-to-day demands—this mindset threatens future viability.● 🧠 Intellect Isn’t Enough—Action Is Required: Even highly intelligent partners struggle to act on succession plans without outside support and structure.● 💼 Build a Business, Not Just a Book: Firms that are sustainable and transferable command higher valuations and are more attractive to buyers or internal successors.Quotes from Daniel McMahon:● “I’m not here to outsmart my clients. I’m here to help them take a step forward.”● “Governance isn’t just board minutes—it’s a cultural process that drives alignment.”● “If your firm is sustainable and transferable, you’re not just selling a practice—you’ve built an enterprise.”🔗 Conclusion:Succession doesn’t start when you’re ready to exit—it starts when you decide to build a firm that can thrive without you. Learn more about your ad choices. Visit megaphone.fm/adchoices

    25 min

  5. 12/18/2025

    Succession Planning and Business Exit Strategies for Entrepreneurs

    What happens when a corporate dealmaker hits midlife and chooses law school over a sports car? In this episode, discover how attorney Kevin Timson brings deep business insight to legal strategies that help entrepreneurs and auto dealers plan smarter exits and succession.In this episode of Sterling Insights, guest host Peter Florio sits down with Kevin Timson, an attorney at ArentFox Schiff with over 25 years of combined business and legal experience. Together, they explore succession planning, business exits, and long-term legal strategy for entrepreneurs and automotive dealership owners, sharing valuable insights and practical tips for listeners. Kevin draws from his unique path—from business development to boutique law firms to a national firm—offering real-world advice on navigating ownership transitions, valuations, and family business complexities. This episode is a must-listen for advisors, attorneys, and business owners planning for the future, providing both knowledge and tools to navigate this critical phase of business life.Key Takeaways:● 🔁 Succession Planning Isn’t One-Size-Fits-All: Kevin explains how every succession plan must be tailored to the family dynamics, asset types, and future goals of each business owner.● 💼 Valuation is More Art Than Science: Owners often cling to fixed numbers, but Kevin emphasizes that value is ultimately what a willing buyer and seller agree on.● 🧠 Business Owners Struggle to Zoom Out: Many entrepreneurs get stuck in day-to-day operations and neglect long-term planning—until it's too late.● 🧭 Trust is the Cornerstone of Advisory Relationships: Whether attorney or wealth advisor, success starts with mutual trust and a shared goal.● 🛠️ Your Legal Partner Should Be a Problem-Solving Sherpa: Kevin sees himself as a flexible problem-solver who listens first and then curates legal strategies from a vast network of resources.Quotes from Kevin Timson:● "You never step in the same river twice—every business transition is unique."● "The best valuation is what a willing buyer and a willing seller can agree on."● "I aim to be a continuity-of-care provider—someone clients can trust across every phase of the journey."🔗 Conclusion:Whether you're a business owner nearing retirement or an advisor guiding clients through transitions, this episode delivers essential wisdom on how to plan with clarity, confidence, and the right team beside you.Connect with Kevin:Website:  https://www.afslaw.com/attorneys/kevin-timsonWith Your Guest Host Peter Florio:Peter F. Florio, CFP®, CLU®, ChFC®, CExP™, CLTC®, is the Founder and Managing Partner of The Florio Wealth Management Group in Westbury, NY. With nearly 40 years of experience, he provides comprehensive wealth, tax, and financial planning for high-net-worth individuals and business owners across the country.Connect with Peter:Website: https://www.floriowmg.comLinkedIn: https://www.linkedin.com/company/florio-wealth-management-group/Facebook: https://www.facebook.com/floriowmgCalendly: https://calendly.com/floriowmg Learn more about your ad choices. Visit megaphone.fm/adchoices

    24 min

  6. 12/17/2025

    Fearless Finance for High-Net-Worth Clients: Planning Beyond Investments

    Most people obsess over hot stock tips — but what if true financial peace came from planning for what really matters? This episode challenges conventional thinking and offers a new lens on wealth, risk, and legacy. In this episode of Sterling Insights, Roger sits down with Laura Rehbein, Private Wealth Advisor and Founder of Impavid Wealth Advisors. Together, they explore how to bring clarity and confidence to high-net-worth financial planning, sharing valuable insights and practical tips for listeners. Laura draws from her 30 years of experience to discuss emotional blind spots, legacy planning, digital assets, and the dangers of "bad math", offering actionable advice for affluent professionals and retirees. This episode is a must-listen for advisors, wealth builders, and those navigating complex financial lives, providing both knowledge and tools to navigate this important subject. Key Takeaways: ● 💼 Planning Is More Than Investing: True wealth management means planning for life events, risks, and what money needs to do for you — not just watching the markets. ● 📚 Why “Throw It in a Pile” Works: Laura’s simple but powerful method helps uncover forgotten accounts, misaligned goals, and missing documents. ● 🧠 Emotions Drive Money Decisions: Even smart, successful people struggle with fear and uncertainty around money — acknowledging that is key to great planning. ● 🐾 Don't Forget the Pets: Estate planning isn't complete without considering pets and digital assets — yes, even your Facebook page. ● ⚖️ Balance Assets for Flexibility: Too much in retirement accounts can cause tax headaches later. Strategic asset location matters. Quotes from Laura Rehbein: ● “Measure money against the job it needs to do someday — and keep measuring, because life changes.” ● “People think they need investments. What they really need is clarity.” ● “You can have all the money in the world and still have a financial train wreck if you don’t plan beyond the numbers.” 🔗 Conclusion: If you're still focused only on returns, you're missing the real value of planning. This episode will help you think bigger — and smarter — about wealth. Connect with Laura: LinkedIn: https://www.linkedin.com/in/laurarehbein/ LinkedIn: https://www.linkedin.com/company/impavid-wealth-advisors-a-private-wealth-advisory-practice-of-ameriprise-financial-services-llc  Facebook: https://www.facebook.com/ImpavidWealthAdvisors 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

    34 min

  7. 12/11/2025 · BONUS

    How Business Owners Use Infinite Banking to Build Wealth and Access Capital

    Are you a business owner wondering how to build wealth without giving up control of your cash? This episode will change how you think about financing, investing, and navigating economic uncertainty.In this episode of Sterling Insights, guest host Charles Trakas sits down with M.C. Laubscher, founder and wealth strategist at Producers Wealth. Together, they explore how business owners can use infinite banking to grow and protect their wealth, while maintaining access to capital. M.C. draws from his extensive experience as an investor, entrepreneur, and immigrant success story to discuss the real challenges business owners face—like liquidity, control, and taxes—offering actionable strategies for long-term financial independence.This episode is a must-listen for entrepreneurs, financial advisors, and business owners, providing both insights and tools to take control of cash flow and create sustainable wealth.Key Takeaways:● 💸 Be Your Own Bank: Infinite banking helps business owners keep control of their capital while still getting growth and protection.● 🔄 Cash Flow Seasons: Every business has high and low seasons—this strategy helps smooth cash flow in “winter” months.● 🔐 Keep Liquidity & Control: Traditional diversification often locks up money—this approach keeps your money accessible.● 🧾 Tax Efficiency: Proper structuring with life insurance can unlock tax advantages that boost net worth.● 💼 Real-World Application: M.C. shares how his clients leverage these tools to fund real estate, business expansion, and personal goals—even during crises like the pandemic.Quotes from M.C. Laubscher:● "The IRS code is literally a playbook that tells you how to pay the least amount of taxes—legally."● "If you don’t understand the rules of the banking system, you’re just a piece on someone else’s board."● "Infinite banking gave me certainty when everything else collapsed—real estate, oil, even cash flow."🔗 Conclusion:Infinite banking isn't just a theory—it’s a practical strategy for business owners who want more control, better tax outcomes, and greater flexibility to scale. If you want to protect and supercharge your assets, this episode is your blueprint.Connect with M.C.:Website:  www.getwealthforsure.comWith Your Guest Host Charles Trakas:Charles Trakas is the President of Trakas Financial, LLC, Senior Wealth Advisor with Redwood Private Wealth, and Founder of Proactive Tax Reductions. For over 26 years, he has helped high-net-worth individuals and business owners grow, protect, and transfer wealth through tax-efficient strategies. A lifelong entrepreneur and financial coach, Charles collaborates with CPAs, attorneys, and advisors to deliver comprehensive planning that minimizes taxes and maximizes long-term financial success.Connect with Charles:Website:  https://proactivetaxreductions.com/about-us/ LinkedIn:https://www.linkedin.com/in/businessownertaxreductionadvisor/ Facebook Business:https://www.facebook.com/TrakasFinancial  Facebook Personal:https://www.facebook.com/profile.php?id=100011447285280New boost Learn more about your ad choices. Visit megaphone.fm/adchoices

    26 min

  8. 12/10/2025

    Purpose-Driven Wealth Planning for High-Net-Worth Clients

    What happens when values and financial advice don’t align? This episode explores how purpose-driven planning can reshape the advisor-client relationship—and why it matters more than ever for high-net-worth families. In this episode of Sterling Insights, Roger sits down with Darryl Lyons, co-founder of PAX Financial Group and a Certified Financial Planner. Together, they explore purpose-driven financial planning through a Judeo-Christian lens, sharing valuable insights and practical tips for advisors and clients alike. Darryl draws from his extensive experience working with business owners and high-net-worth families to discuss value alignment, charitable giving strategies, and navigating today’s complex economic environment, offering actionable advice for financial professionals and faith-driven investors. This episode is a must-listen for advisors who serve high-net-worth clients and want to lead with purpose, providing both knowledge and tools to navigate this important subject. Key Takeaways: ● ✝️ Aligning Faith and Finance: Why purpose-driven planning resonates with clients who want their investments to reflect their core values. ● 💼 Ideal Client Profile: How PAX Financial serves business owners with $10M+ net worth, especially those approaching succession. ● 📈 Net Asset Flow as Growth Metric: Why Darryl prefers tracking organic AUM growth over total assets. ● 🎁 Strategic Generosity: How donor-advised funds and thoughtful giving strategies can help clients give meaningfully—and tax-efficiently. ● 🧩 Navigating ESG & Proxy Voting: A candid look at how ESG investing intersects (and conflicts) with Judeo-Christian values. Quotes from Darryl Lyons: ● "He didn’t want to wrestle with the why of giving—he wanted someone who already believed in it, and would focus on how to do it well." ● "If you're using the Lord’s name just to garner business, that’s using it in vain—and I take that seriously." ● "We charge a modest fee because people value what they pay for—and we want them to take action." 🔗 Conclusion: Purpose-driven financial planning isn’t just about performance—it’s about trust, alignment, and helping clients live out their values through their wealth. Connect with Darryl: Website:  https://paxfinancialgroup.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

    29 min
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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.

Information

  • Creator
    Roger Silk
  • Years Active
    2024 - 2025
  • Episodes
    81
  • Rating
    Clean
  • Copyright
    © Copyright 2024 Sterling Insights. Roger Silk. All Right Reserved.
  • Show Website
    Sterling Insights

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