Sterling Insights cover art

Sterling Insights

Sterling Insights

By: Roger Silk
Listen for free

About this listen

 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
Episodes
  • Bonus: Cost Segregation Secrets to Keep More of Your Money

    Bonus: Cost Segregation Secrets to Keep More of Your Money
    Nov 20 2025
    Think cost segregation is just for big-time developers? Think again. This episode reveals how one strategy can unlock massive tax savings—even for everyday real estate investors and medical professionals.In this episode of Sterling Insights, guest host Charles Trakas sits down with David Wiener, CEO of Cash Flow Strategies and one of the top cost segregation experts in the country. Together, they explore how cost segregation, bonus depreciation, and R&D credits can significantly boost cash flow and reduce tax burdens, sharing valuable insights and practical tips for listeners. David draws from his extensive experience helping doctors, dentists, and real estate investors uncover hidden savings, offering actionable advice for financial advisors and high-net-worth clients seeking smarter tax strategies.This episode is a must-listen for advisors, CPAs, real estate professionals, and investors—providing both knowledge and tools to navigate this powerful (and often misunderstood) strategy.Key Takeaways:● 💸 Cost Seg Isn’t Just for Commercial Giants: Even a single-family rental can qualify for this tax strategy.● 🧱 Break Down the Building: Learn how to reclassify assets for faster depreciation—and bigger deductions.● 🧾 Bonus Depreciation Is Back (And Permanent): The “Big Beautiful Bill” makes this a golden opportunity for real estate owners.● 🧠 Avoid DIY Pitfalls: Cheap cost seg studies can cost you more in audits. Engineering-based reports are IRS-recommended.● 🔬 R&D Credits Expanded: More industries (including IT) can now qualify—and the credits are available upfront.Quotes from David Wiener:● “It’s your money—keep more of it.”● “You wouldn’t price shop for a brain surgeon. Why do it for your taxes?”● “We’ve done 50,000+ studies and never triggered an audit.”🔗 Conclusion:Cost segregation isn’t just a tax tool—it’s a cash flow supercharger. Advisors and investors who understand it can unlock serious financial leverage.Connect with David:Website: https://costsegregation.infoYouTube: https://youtube.com/cashflowstrategiesincInstagram: https://www.instagram.com/david.wienerConnect with Charles Trakas: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 Learn more about your ad choices. Visit megaphone.fm/adchoices
    Show More Show Less
    21 mins
  • Episode 40: Personal CFO Strategies for High-Net-Worth Planning

    Episode 40: Personal CFO Strategies for High-Net-Worth Planning
    Nov 19 2025
    What if the biggest financial risks you face aren’t while building wealth—but when you start spending it? In this episode of Sterling Insights, Roger sits down with Erik Brenner, CFP®, President & CEO of Hilltop Wealth and Tax Solutions. Together, they explore the complexities of transitioning from wealth accumulation to wealth distribution, sharing valuable insights and practical strategies for listeners. Erik draws from over 30 years of experience to discuss tax mitigation, retirement pitfalls, the Personal CFO model, and the challenges facing today’s high‑net‑worth families, offering actionable advice for anyone navigating the modern financial landscape. This episode is a must-listen for high‑net‑worth individuals, business owners, physicians, and advisors seeking deeper planning insights, providing both knowledge and tools to make smarter decisions on the way down the financial mountain. Key Takeaways: ● 💼 Retirement Isn’t What It Used to Be: Today’s retirees face far more complexity—fewer pensions, more choices, and higher stakes. ● 🧭 The “Coming Down the Mountain” Risk: Most financial mistakes happen during the distribution phase, not the accumulation phase. ● 🧾 Tax Mitigation - Tax Planning: Erik explains why minimizing taxes this year—not deferring them—is essential for high-income and high‑net‑worth individuals. ● 🏛️ The Power of the Personal CFO Model: Comprehensive planning that integrates investments, tax, and estate strategy leads to better long-term outcomes. ● 🌅 Secure Act Changes Everything: New laws have reshaped inheritance, RMDs, and Roth strategy—making guidance more important than ever. Quotes from Erik Brenner: ● “It’s not your parents’ or grandparents’ retirement anymore.” ● “Most deaths in mountain climbing happen on the way down—and financially, it’s no different.” ● “Tax mitigation means reducing tax today and never paying it back—not just kicking it down the road.” 🔗 Conclusion: Navigating wealth today requires more than investment management—it requires a coordinated, strategic Personal CFO guiding every major financial decision. Connect with Erik: Website: https://hilltopwealthtax.com/ LinkedIn: https://www.linkedin.com/in/erikbrenner/ LinkedIn: https://www.linkedin.com/company/hilltopwealthtax/ Facebook: https://www.facebook.com/hilltopwealthtax Instagram: https://www.instagram.com/hilltopwealthtax/ YouTube: https://www.youtube.com/@HilltopWealthTaxSolutions 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
    Show More Show Less
    26 mins
  • Bonus: From Chaos to Clarity: Mastering the Family Business Exit

    Bonus: From Chaos to Clarity: Mastering the Family Business Exit
    Nov 12 2025
    70% of family businesses fail to transition successfully — what if the right conversation could change that? Discover how proactive planning, people-first strategies, and a clear roadmap can turn succession chaos into clarity.In this episode of Sterling Insights, guest host Ray O’Connell sits down with Chuck Cooper the founder of Whitewater Consulting, a seasoned business consultant specializing in HR, succession, and exit planning for family-owned and mid-sized businesses. Together, they explore the hidden pitfalls of business succession, sharing valuable insights and practical tips for listeners. The guest draws from decades of experience to discuss why most succession plans fail, how to navigate emotionally charged family dynamics, and how to build a roadmap that secures both legacy and value.This episode is a must-listen for business owners, financial advisors, and professionals working with family enterprises, providing both knowledge and tools to navigate this critical stage of business growth and transition.Key Takeaways:● 🔄 Succession Is a Process, Not an Event: Business owners should start planning 3–5 years ahead, not 6–12 months before exiting.● 🧭 Clarity Starts with Conversations: Open, facilitated conversations among family members are key to aligning vision and expectations.● 💼 Value Is More Than EBITDA: Up to 80% of business value comes from human, structural, customer, and cultural capital — not financial statements.● 🧠 Advisors Matter: Succession planning requires a trusted team — legal, financial, HR, and coaching professionals all play a role.● 📚 The Tools Are There — Use Them: The guest’s book and toolkit provide business owners a DIY path or support for guided implementation.Quotes from the Chuck:● “70% of business owners we surveyed had no succession or exit plan in place.”● “Most of your business’s value isn’t on your balance sheet — it’s in your people, your systems, and your relationships.”● “Succession isn’t the end — it’s the start of a new chapter. The sooner you plan, the better your story ends.”🔗 Conclusion:Business owners can’t afford to wait. Whether you're focused on preserving your legacy, protecting your team, or maximizing your exit value, thoughtful succession planning is the bridge between what your business is today — and what it can become.Connect with Chuck:Website: https://whitewaterconsulting.net/With Your Guest Host Ray O'Connell:Ray O’Connell, Accredited Investment Fiduciary® (AIF®), is founder and Managing Director of Altus Wealth Strategies, dba Altus Wealth and Tax. Altus Wealth and Tax uses a Proactive and Holistic Planning and Tax / Capital Gains Minimization process backed by a team of 50+ Family Office specialists. We have been in business for over 30 years, located in the Southeast, and work nationally. O’Connell has taught hundreds of advisors the principles of integrating tax planning strategies with investments and insurance. He has presented programs to physician groups, business owners and high net worth. He is also an author.Connect with Ray:Email: Ray@AltusWealthAndTax.comWebsite: https://altuswealthstrategies.com/ Learn more about your ad choices. Visit megaphone.fm/adchoices
    Show More Show Less
    24 mins
No reviews yet
In the spirit of reconciliation, Audible acknowledges the Traditional Custodians of country throughout Australia and their connections to land, sea and community. We pay our respect to their elders past and present and extend that respect to all Aboriginal and Torres Strait Islander peoples today.