Episodes

  • Bonus: From Farm to FinPro: Holistic Accounting for Blue-Collar Clients

    Bonus: From Farm to FinPro: Holistic Accounting for Blue-Collar Clients
    Jan 15 2026
    What happens when a small-town kid from a dairy farm builds a modern, cloud-based accounting firm serving blue-collar business owners nationwide? You get a fresh take on holistic financial services that’s rooted in hard work and real-world impact.In this episode of Sterling Insights, guest host Charles Trakas sits down with Cody Roos, Enrolled Agent and founder of FinPro Accounting. Together, they explore how to build a full-service, client-first accounting firm tailored to the unique needs of blue-collar entrepreneurs and financial professionals. Cody draws from his diverse background in farming, financial services, and tax planning to discuss the gaps small business owners face in accounting, payroll, and tax compliance, offering actionable advice for advisors and entrepreneurs alike. This episode is a must-listen for advisors, accountants, and business owners who want to deliver greater value while scaling smartly.Key Takeaways: 💼 Holistic Service Wins: Cody shares how adding tax, payroll, and bookkeeping services filled critical gaps for clients—and grew his business. 🧠 AI as a Study Partner: He credits ChatGPT with helping him pass the Enrolled Agent exam quickly and effectively. 🧰 Supporting Blue-Collar Entrepreneurs: Many clients just want to do great work—Cody handles the rest so they can grow. 🌐 Cloud-Based, Nationwide Firm: Learn how FinPro serves clients across the U.S. with zero paper and 100% trust. 📊 Tiered Pricing = Smarter Scaling: A client told Cody he wasn’t charging enough—now he offers three tiers that align value with service. "I don’t necessarily think I’ve become an expert in any one area—my focus is adding as much value as possible." "Every person you meet knows something you don’t know." "I never want to become a tax return factory. Quality is everything." Quotes from Cody Roos:Connect with Cody:Website: https://www.finproaccounting.com/wp/wp-admin/LinkedIn: https://www.linkedin.com/in/cody-roosConnect 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=100011447285280🔗 Conclusion:Whether you serve farmers, contractors, or financial advisors, delivering integrated, high-trust accounting services can transform your client relationships—and your business. Learn more about your ad choices. Visit megaphone.fm/adchoices
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    30 mins
  • Episode 48: Succession Planning for Financial Advisors: How to Build Value and Transition Clients

    Episode 48: Succession Planning for Financial Advisors: How to Build Value and Transition Clients
    Jan 14 2026
    What happens to your clients, your team, and your business if something happens to you tomorrow? This episode dives into why every financial advisor needs a documented succession plan—before it’s too late.In this episode of Sterling Insights, Roger sits down with PJ McDaniel, Partner at Socium Advisors and a leader in advisor growth strategy within Northwestern Mutual. Together, they explore succession planning for financial advisors, sharing valuable insights and practical tips for listeners. PJ draws from his extensive experience in wealth management and M&A to discuss the demographic shift in the industry, the risks of poor planning, and how to transition client relationships and enterprise value effectively, offering actionable advice for advisors working with high-net-worth clients. This episode is a must-listen for advisors looking to protect their legacy, their clients, and their families, providing both knowledge and tools to navigate this critical business decision.Key Takeaways:● Most Advisors Lack a Plan: Up to 94% of advisors don’t have a documented succession plan—leaving clients and families vulnerable.● Start Early: Succession planning isn’t just for retirement; it's risk management in case of unexpected events.● Trusted Partnerships Matter: A successful transition hinges on finding the right next-gen partner and building trust over time.● Valuation Confusion: Many advisors don’t fully understand what their business is worth or how M&A dynamics affect value.● Culture Fit First: When considering a merger or acquisition, cultural alignment is more important than revenue or AUM.Quotes from PJ McDaniel:● “It’s like having a will—you hope you never need it soon, but if you do and don’t have it, the consequences can be huge.”● “The most successful transitions we’ve seen are built over two to three years, not two to three months.”● “If you’re not spending most of your time with clients, something needs to change—that’s where we come in.”🔗 Conclusion:If you’re an advisor without a clear, written succession plan—or just want a second opinion—this episode offers the clarity and next steps you need.Connect with PJ:Website: https://sa.nm.com/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
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    30 mins
  • Bonus: How Businesses Win Big in Insurance Recovery and Legal Disputes

    Bonus: How Businesses Win Big in Insurance Recovery and Legal Disputes
    Jan 8 2026
    Think you understand how insurance companies operate behind the scenes? Think again. This episode dives deep into how businesses can protect themselves—and win—when insurers don't play fair.In this episode of Sterling Insights, guest host Peter Florio sits down with Evan Schwartz, a nationally recognized attorney and insurance recovery expert. Together, they explore the complex world of insurance claims litigation and recovery, sharing valuable insights and practical tips for listeners. Evan draws from over 30 years of experience to discuss what businesses often misunderstand about legal battles with insurers, offering actionable advice for advisors, entrepreneurs, and business owners. This episode is a must-listen for professionals who work with high-net-worth clients or manage risk, providing both knowledge and tools to navigate this important subject.Key Takeaways:● 📈 Understanding Insurance Recovery: Learn how businesses can fight back when insurance companies deny or delay legitimate claims.● 💼 From Law to Business: Why many lawyers struggle running a firm—and what Evan did differently to build a successful, client-focused practice.● 🧠 Empathy in Advocacy: Discover how emotional intelligence and listening deeply can set legal professionals apart.● 🧩 Big Picture Strategy: Why Evan believes that lawyers must stop being “just lawyers” and start thinking like business owners.● ⚖️ Landmark Legal Action: Hear how Evan’s class action lawsuit reshaped a national insurance company’s claims practices—and helped thousands of policyholders.Quotes from Evan Schwartz:● “Clients want to spend as little time and money with their lawyer as possible—and that’s the truth.”● “Empathy is one of the great keys of life, especially for a lawyer. You need to truly listen with intent.”● “You can learn about many different professions as a lawyer without actually being in those professions—that’s what keeps me engaged.”🔗 Conclusion:Whether you're advising clients, running a business, or navigating your own insurance dispute, this episode offers a front-row seat to the mindset and strategy behind real legal impact.Connect with Evan:Firm Website: https://schlawpc.com/LinkedIn Profile: https://www.linkedin.com/in/evansschwartz/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/floriowmgNew boost Learn more about your ad choices. Visit megaphone.fm/adchoices
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    26 mins
  • Episode 47: How Tech and Crypto Professionals Can Save Millions in Taxes

    Episode 47: How Tech and Crypto Professionals Can Save Millions in Taxes
    Jan 7 2026
    What if a few smart moves could save you millions in taxes on your tech equity or crypto gains? This episode dives into the real strategies high-earning professionals need to know—but most don’t.In this episode of Sterling Insights, Roger sits down with a seasoned financial planner who specializes in working with high-net-worth professionals in tech and crypto. Together, they explore advanced tax planning strategies, sharing valuable insights and practical tips for listeners. Drawing from extensive experience with clients holding concentrated equity and crypto portfolios, the guest discusses how to manage equity compensation, minimize taxes, and plan charitable giving. This episode is a must-listen for tech and crypto professionals sitting on major unrealized gains, offering both clarity and tools to take control of their financial future.Key Takeaways:● 💼 Equity Compensation 101: Understand the differences between RSUs, ISOs, and NSOs—and why timing matters more than you think.● 🧾 AMT Pitfalls: Learn how the Alternative Minimum Tax affects stock option planning and what to do before you exercise.● 💸 CRT Strategy: Discover how a Charitable Remainder Trust can help you diversify and generate income without triggering a tax bomb.● 🪙 Crypto Planning: Why crypto gains are taxable, how to manage your holdings, and the importance of getting your tokens "into the system."● 🧠 Risk & Goals Alignment: How to evaluate your wealth not just by numbers, but by what it allows you to do—from buying real estate to funding early retirement.Quotes from the guest:● “We always start with: What do you want your money to do for you?”● “You can look on paper and think, ‘I’ve got $3 million in stock,’ but if you don’t plan, you might only keep half.”● “It’s not about just paying less tax—it’s about using that money to fuel the life you want.”🔗 Conclusion:If you're holding significant equity or crypto and want to avoid massive tax bills while securing your financial future, this episode is your roadmap.Connect with Jennifer:Website: https://www.modernfamilyfinance.com/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
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    36 mins
  • Epiisode 46: Building a $25M+ Minimum Family Office for First-Gen Entrepreneurs

    Epiisode 46: Building a $25M+ Minimum Family Office for First-Gen Entrepreneurs
    Dec 31 2025
    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
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    30 mins
  • Bonus: Estate Planning for Business Owners: Protect Assets, Cut Taxes, Build Legacy

    Bonus: Estate Planning for Business Owners: Protect Assets, Cut Taxes, Build Legacy
    Dec 30 2025
    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
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    45 mins
  • Episode 45: How Top Advisors Scale with Purpose Using the 80/20 Rule and Practice Management

    Episode 45: How Top Advisors Scale with Purpose Using the 80/20 Rule and Practice Management
    Dec 24 2025
    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
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    32 mins
  • Bonus: Succession, Governance & Growth: How CPA Firms Build Transferable Value

    Bonus: Succession, Governance & Growth: How CPA Firms Build Transferable Value
    Dec 23 2025
    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
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    25 mins