Sterling Insights

Market Domination

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. 2D AGO

    Episode 50: Tax-Efficient Strategies for Concentrated Stock & Roth Conversions

    How do high-net-worth investors reduce concentrated stock risk and taxes—without blowing up their long-term plan?In this episode of Sterling Insights, Roger sits down with Gary Pattengale, CFP®, CPA, Senior Vice President and Advanced Planning Specialist at Mesero Wealth Management. Together, they explore tax-efficient strategies for managing concentrated stock positions, Roth conversions, and holistic wealth planning for high-net-worth families. Gary draws from over 25 years of experience to discuss concentration risk, tax-aware diversification strategies, and advanced planning techniques, offering actionable advice for investors, executives, and advisors navigating complex financial decisions. This episode is a must-listen for high-net-worth individuals and financial professionals seeking smarter, more integrated planning strategies.Key Takeaways:● Concentration Risk Starts Around 10%: While 10% in a single stock is a common rule of thumb, true risk tolerance depends on age, goals, income sources, and overall net worth.● Create a Rules-Based Liquidation Strategy: Removing emotion from selling appreciated stock by setting pre-defined triggers can help investors diversify systematically and tax-efficiently.● Roth Conversions Require Careful Modeling: Conversions can increase lifetime wealth—but hidden “tax torpedoes” like Social Security taxation, capital gains brackets, and Medicare premiums must be considered.● Integrate Tax, Estate, and Investment Planning: The most effective strategies align tax efficiency, legacy intent, and portfolio design into one coordinated plan.● Advanced Tools Improve Planning Outcomes: Modern tax and financial planning software allows advisors to model “what-if” scenarios efficiently, enabling dynamic, data-driven decisions.Quotes from Gary Pattengale:● “Taxes are important—but first we assess the concentration risk. What happens if that stock drops 40 to 60%?”● “Once the rule is triggered, we execute. It takes the emotion out of it.”● “Roth conversions aren’t for everybody. You really have to analyze the full tax impact before you act.”True wealth management isn’t about chasing returns—it’s about integrating tax strategy, risk management, and long-term planning into one cohesive approach that protects and grows wealth across generations.Connect with Gary:Website:  https://www.mesirow.com/homeLinkedIn:  https://www.linkedin.com/in/gary-pattengale-cfp%C2%AE-3806b822/Connect with Roger:Website:  https://www.sterlingfoundations.comFacebook:  https://www.facebook.com/sterlingfoundations/Twitter:  https://x.com/SterlingFndMgt?mx=2LinkedIn:  https://www.linkedin.com/company/sterling-foundation-management-llc/ Learn more about your ad choices. Visit megaphone.fm/adchoices

    27 min

  2. MAR 5

    Bonus: League City Insurance Agency Home Auto Life Umbrella Farmers Insurance

    In this episode of Sterling Insights, Mike Agol sits down with Angie Smith, Agency Owner at Farmers Insurance and full-service risk protection specialist. Together, they explore how to properly protect your assets, family, and legacy through strategic insurance planning, sharing valuable insights and practical tips for listeners. Angie draws from her extensive experience to discuss common coverage gaps, umbrella policies, lawsuits, and misconceptions about “cheap” insurance, offering actionable advice for homeowners, business owners, and high-net-worth families. This episode is a must-listen for anyone building wealth who wants to make sure it’s properly protected, providing both knowledge and tools to navigate this critical subject. Key Takeaways: ● Value Over Price: The cheapest policy is rarely the best policy. Proper coverage protects everything you’ve worked hard to build. ● Umbrella Policies Matter: An umbrella policy is one of the most affordable ways to shield assets from major lawsuits and liability claims. ● Coverage Gaps Are Common: Jewelry, small business exposures, and liability risks are often underinsured or misunderstood. ● Advisors Should Collaborate: Insurance and financial advisors must work together to fully protect a client’s portfolio. ● Insurance Is Personal: True service goes beyond policies — it means showing up during freezes, hurricanes, and life’s toughest moments. Quotes from Angie Smith: ● “On a bad day, I want to make sure what you’ve built is still protected.” ● “An umbrella policy is the cheapest attorney you’ll ever have protecting your assets.” ● “We don’t just sell a policy — we sell value and proper protection.” Building wealth is only half the equation — protecting it is what secures your legacy. Learn more about your ad choices. Visit megaphone.fm/adchoices

    16 min

  3. FEB 25

    Fan Fav: Centered Leadership in Wealth Management

    How do you build a client-first financial firm from the ground up—and keep it human at scale?In this episode of Sterling Insights, Roger sits down with Susie Cranston, President and COO of Crescent, a $65+ billion multifamily office and private investment firm. Together, they explore what it takes to deliver deeply personalized wealth management at scale, sharing valuable insights and practical tips for leaders, founders, and families navigating complex financial landscapes. Susie draws from decades of experience at McKinsey, First Republic, and now Crescent to discuss the power of culture, the evolution of client expectations, and how RIAs are reshaping wealth advisory. This episode is a must-listen for ultra-high-net-worth families, founders approaching liquidity, and professionals building modern client-first financial firms, providing both knowledge and tools to navigate this important subject. Key Takeaways:● 💼 Client-First DNA: Crescent’s model was literally built by clients, for clients, offering flexibility that traditional banks can’t match.● 🏛️ RIAs vs. Banks: Regulatory constraints limit the services banks can provide—RIAs like Crescent offer broader, deeper support in tax and private investing.● 🔍 Fit Over Size: Crescent’s ideal client isn’t just about net worth—it’s about mindset and the desire for holistic, customizable support.● 🧑‍🤝‍🧑 Team Culture Drives Client Success: Exceptional service starts with exceptional culture—Crescent prioritizes servant leaders and long interview processes to build elite teams.● 📈 Scale Matters—for the Right Reasons: Being “industrial-grade” at $50B+ AUM allows for better infrastructure, tech, and access—without losing the boutique client feel. Quotes from Susie Cranston:● “Our origin story is unique—we were built by clients, for clients.”● “You can’t outsource culture. It’s the best predictor of organizational success.”● “We aim to be the co-pilot in a family's financial life—scaling with them across the journey.” 🔗 Crescent offers what most firms can’t: customized service backed by enterprise-level infrastructure. Learn more at crescentcapital.com and tune into this episode to see what the future of wealth management looks like. Learn more about your ad choices. Visit megaphone.fm/adchoices

    25 min

  4. FEB 12

    Bonus: Tax Strategy, IRS Relief, and Building a Virtual CPA Firm

    What if your tax problem isn’t actually a tax problem—but a bookkeeping one? Or what if the IRS doesn’t need to be feared, just better understood? This episode dives into the overlooked strategies and real-world solutions that could change the financial future of high-income earners and business owners.In this episode of Sterling Insights, guest host Tracy McCary sits down with Adam Remis, CPA and founder of The Accounting Doctor. Together, they explore how advanced tax strategy and resolution can transform a client’s financial—and even physical—well-being, sharing valuable insights and practical tips for listeners. Adam draws from his 28+ years of experience to discuss how to effectively handle tax debt, avoid costly mistakes, and optimize taxes for high earners, offering actionable advice for wealth advisors, business owners, and high-income individuals. This episode is a must-listen for advisors with high-net-worth clients or anyone seeking smarter, proactive ways to tackle tax complexity.Key Takeaways:● Tax Resolution is More Than Numbers: Addressing tax debt isn’t just financial—it can dramatically improve a client’s mindset, health, and quality of life.● Don't DIY the IRS: Trying to resolve issues with the IRS yourself can backfire. Adam explains why professional representation matters.● Virtual Firms Are Winning: Adam shares how his remote model helps him recruit top talent and serve clients nationwide without geographic limitations.● Tax Misconceptions Hurt Clients: Many people unknowingly overpay or misreport—leading to years of unnecessary stress or tax court battles.● Advanced Strategies for High Earners: Adam reveals how clients earning $400k+ can use overlooked strategies to reduce income and capital gains taxes.Quotes from Adam Remis:● "Helping clients resolve their IRS debt isn’t just about money—it’s about lifting a massive psychological burden."● "Doing it yourself with the IRS is like representing yourself in criminal court. You need an expert in your corner."● "The details matter. We’ve saved clients tens of thousands simply by doing the digging their previous CPAs didn’t."Whether you're an advisor looking to better support high-net-worth clients or someone navigating complex tax issues yourself, this episode offers a rare behind-the-scenes look at how smart strategy—and the right partner—can make all the difference.Connect with Adam:Website:  https://www.theaccountingdoctor.comLinkedIn:  https://www.linkedin.com/in/adam-b-remis-msim-cpa-l-i-o-n-b354b1/ Learn more about your ad choices. Visit megaphone.fm/adchoices

    20 min

  5. FEB 10

    Bonus: Understanding Employment Law: Workplace Rights & Wrongful Termination

    Think your job termination was unfair—and maybe even illegal? You’re not alone. But the difference between “unfair” and “unlawful” is more complex than most people realize. This episode dives deep into what employees (and employers) need to know about their rights in the workplace.In this episode of Sterling Insights, guest host Peter Florio sits down with employment attorney Raymond Nardo, a seasoned legal expert with over 30 years of experience in labor and employment law. Together, they explore the realities of employment law, sharing valuable insights and practical tips for listeners. Raymond draws from his extensive experience to discuss wrongful termination, wage and hour disputes, discrimination claims, and the misconceptions employees often have about their rights, offering actionable advice for anyone navigating workplace challenges. This episode is a must-listen for professionals, business owners, HR managers, and employees facing tough job transitions, providing both knowledge and tools to understand and protect your rights.Key Takeaways:● The Harsh Truth About Employment at Will: Most private-sector employees can be terminated for any reason—or no reason at all—unless specific legal protections apply.● Unfair ≠ Illegal: Many workplace terminations may feel unfair but don't meet the legal threshold for wrongful termination or discrimination.● Wage & Hour Laws Are a Legal Minefield for Employers: Employers often violate wage laws without realizing it—missing notices, misclassifying employees, or improperly calculating overtime.● Discrimination Protections Exist—but Proof Is Key: Laws protect against discrimination based on race, gender, age, and more, but proving it can be difficult and requires strong documentation.● Legal Action Isn’t the Only Path: Sometimes, a well-crafted letter or negotiation can resolve disputes without litigation, especially when handled by an experienced advocate.Quotes from Raymond Nardo:● "Law and justice are distant cousins when it comes to employment law."● "Nine out of ten people who call me don’t have a case—because employment at will gives employers broad leeway."● "Even if we don’t win a case, we raise awareness—and that can change how employers operate going forward."🔗 Conclusion:Whether you’re an employee wondering if your termination was legal, or an employer navigating compliance, understanding the realities of employment law is critical. This episode sheds light on the rights, risks, and real-world processes behind workplace disputes.Connect with Raymond: Website:  https://www.raynardo.com/With 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

    27 min

  6. FEB 5

    Bonus: How Proactive Legal Strategy Protects Growing Businesses

    Most business owners think of legal help as something they’ll need later—but what if legal strategy could actually drive better decisions and prevent costly problems before they ever appear?In this episode of Sterling Insights, guest host Seth Krussman sits down with Blaine Clooten, attorney at Brownstein Rask and a seasoned advisor to entrepreneurs, executives, and closely held businesses. Together, they explore how legal strategy shows up in real business decisions—not just in the courtroom, sharing valuable insights and practical tips for business owners and advisors alike. Blaine draws from his diverse background in business, litigation, and judging to discuss the risks business owners often overlook, offering actionable advice for those navigating contracts, partnerships, growth, and succession. This episode is a must-listen for entrepreneurs, operating executives, and advisors who support business owners, providing both knowledge and tools to build stronger, more resilient businesses.Key Takeaways:● Proactive vs. Reactive Legal Strategy: Waiting until there’s a problem limits your options—early legal involvement can protect relationships and reduce costs.● Contracts Are Business Marriages: Too many business owners rush contracts without aligning them to their actual goals, leading to future disputes.● Legal Counsel as Strategic Advisor: Good lawyers aren’t just for lawsuits—they're part of your growth and decision-making team.● AI Can’t Replace Legal Judgment: Online tools may generate documents, but they can’t spot your unique risks—or defend you in court.● Annual Legal Checkups Matter: Businesses evolve, and so should your legal documents. Regular reviews help avoid compounding issues.Quotes from Blaine Clooten:● “Most people wait until the problem is at their doorstep—by then, your options are limited and expensive.”● “Signing a contract is like getting married—if you wouldn’t rush that, don’t rush the paperwork that ties your finances to someone else’s.”● “The farther we get with technology, the more important trust-based relationships become in law and business.”🔗 Conclusion:Legal strategy isn’t about slowing you down—it’s about giving you clarity, confidence, and control before problems arise. If you’re building something meaningful, this episode will help you protect it. Connect with Blaine:Website:  https://brownsteinrask.com/attorneys/blaine-clooten YouTube:  https://www.youtube.com/@clootenlawyer LinkedIn:  https://www.linkedin.com/in/clooten/ 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

    1h 3m

  7. FEB 4

    Bonus: From Pharma to Real Estate: Building Trust and Thriving in Commercial & Residential Markets

    What does it really take to thrive in real estate for nearly three decades—through changing markets, interest rate spikes, and personal reinvention? This episode explores how longevity, trust, and adaptability can create a resilient real estate career. In this episode of Sterling Insights, guest host Tracy McCary sits down with Greg Roberts, a seasoned real estate consultant with expertise in both residential and commercial real estate. Together, they explore how building trust and adapting to market shifts has sustained Greg’s business since the mid-90s, sharing valuable insights and practical tips for listeners. Greg draws from his extensive experience to discuss interest rate fluctuations, client evolution, and the shift from cold calls to warm referrals, offering actionable advice for advisors, realtors, and professionals serving high-net-worth individuals. This episode is a must-listen for real estate professionals, financial advisors, and business owners navigating growth in volatile markets, providing both knowledge and tools to navigate this important subject. Key Takeaways: ● Adaptability is Key: Greg transitioned from pharmaceuticals to real estate and grew with the industry—adapting from entry-level buyers to million-dollar clients. ● Trust Drives Referrals: After decades in the business, most of Greg’s leads now come from word of mouth, not advertising. ● Commercial Real Estate as a Growth Lever: Expanding into commercial deals re-energized his business and client relationships. ● Interest Rates are Psychological as Much as Financial: Greg offers context on how consumers perceive 7% rates vs. the recent anomaly of 2–3%. ● Being a "Truth Teller" Pays Off: Greg’s honest approach—telling clients what they need to hear, not just what they want—has built long-term credibility. Quotes from Greg Roberts: ● "I tell you the truth—even if it costs me the listing." ● "You don't know what you don't know—and that's where a trusted advisor matters." ● "I become family to my clients for 30, 60, 90 days during a deal—and then I may not hear from them for two years." 🔗 Conclusion: Whether you're an advisor, real estate pro, or just curious about sustaining success over the long haul, this episode delivers powerful lessons on trust, client service, and staying relevant in a shifting market. Learn more about your ad choices. Visit megaphone.fm/adchoices

    19 min

  8. FEB 3 · BONUS

    Bonus: From Pharma to Real Estate: Building Trust and Thriving in Commercial & Residential Markets

    What does it really take to thrive in real estate for nearly three decades—through changing markets, interest rate spikes, and personal reinvention? This episode explores how longevity, trust, and adaptability can create a resilient real estate career. In this episode of Sterling Insights, guest host Tracy McCary sits down with Greg Roberts, a seasoned real estate consultant with expertise in both residential and commercial real estate. Together, they explore how building trust and adapting to market shifts has sustained Greg’s business since the mid-90s, sharing valuable insights and practical tips for listeners. Greg draws from his extensive experience to discuss interest rate fluctuations, client evolution, and the shift from cold calls to warm referrals, offering actionable advice for advisors, realtors, and professionals serving high-net-worth individuals. This episode is a must-listen for real estate professionals, financial advisors, and business owners navigating growth in volatile markets, providing both knowledge and tools to navigate this important subject.Key Takeaways:● Adaptability is Key: Greg transitioned from pharmaceuticals to real estate and grew with the industry—adapting from entry-level buyers to million-dollar clients.● Trust Drives Referrals: After decades in the business, most of Greg’s leads now come from word of mouth, not advertising.● Commercial Real Estate as a Growth Lever: Expanding into commercial deals re-energized his business and client relationships.● Interest Rates are Psychological as Much as Financial: Greg offers context on how consumers perceive 7% rates vs. the recent anomaly of 2–3%.● Being a "Truth Teller" Pays Off: Greg’s honest approach—telling clients what they need to hear, not just what they want—has built long-term credibility.Quotes from Greg Roberts:● "I tell you the truth—even if it costs me the listing."● "You don't know what you don't know—and that's where a trusted advisor matters."● "I become family to my clients for 30, 60, 90 days during a deal—and then I may not hear from them for two years." 🔗 Conclusion:Whether you're an advisor, real estate pro, or just curious about sustaining success over the long haul, this episode delivers powerful lessons on trust, client service, and staying relevant in a shifting market. Learn more about your ad choices. Visit megaphone.fm/adchoices

    19 min
See All (98)

Trailer

About

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

  • Channel
    Market Domination
  • Creator
    Roger Silk
  • Years Active
    2024 - 2026
  • Episodes
    98
  • Rating
    Clean
  • Copyright
    © Copyright 2024 Sterling Insights. Roger Silk. All Right Reserved.
  • Show Website
    Sterling Insights

More From Market Domination