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Business Insights

Tune into Business 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 Business Insights and empower your advisory practice with the knowledge to succeed.

Latest Episodes:

Bonus: How Proactive Legal Strategy Protects Growing Businesses Feb 05, 2026

Show notes

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-tap
Facebook: https://www.facebook.com/3Dinvesting/
X: https://x.com/BFG_LLC/

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Bonus: From Pharma to Real Estate: Building Trust and Thriving in Commercial & Residential Markets Feb 04, 2026

Show notes

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.

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Bonus: From Pharma to Real Estate: Building Trust and Thriving in Commercial & Residential Markets Feb 03, 2026

Show notes

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.

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Bonus: Avoiding Business Lawsuits: Expert Tips on Commercial Litigation Jan 29, 2026

Show notes

Most business owners fear litigation—but what if the real danger lies in the mistakes made long before a lawsuit is ever filed?
In this episode of Sterling Insights, Seth Krussman sits down with Josi Kovacs, a seasoned commercial litigator from one of the Pacific Northwest’s top boutique firms. Together, they explore how business owners can navigate and avoid complex litigation, sharing valuable insights and practical tips for listeners. Our guest draws from extensive trial and mediation experience to discuss common legal pitfalls, emotional decision-making, and the true cost of waiting too long to call an attorney, offering actionable advice for entrepreneurs, founders, and leaders of closely held businesses. This episode is a must-listen for anyone leading a growing business, providing both knowledge and tools to navigate legal risk before it escalates.
Key Takeaways:
● Litigation Is Rarely the End: Most lawsuits aren’t catastrophic, and there are always paths forward—if you know your options.
● Write It Down: Business owners often skip documentation to preserve relationships, but this can create costly disputes later.
● Call a Lawyer Early: Bringing in litigation counsel before things escalate can help resolve issues before a suit is ever filed.
● Know Your Contracts: Many business leaders sign indemnity clauses without understanding them—until it’s too late.
● Understand the Emotional Toll: Lawsuits aren’t just financial; they’re emotionally draining. Knowing that can shape better decisions.
Quotes from the Josi:
● “Litigation is such a stressful experience—even for seasoned businesspeople.”
● “Litigation isn’t just expensive—it’s emotionally draining. You could be tied up for years, facing someone you no longer trust.”
● “So many problems could be avoided if people just wrote things down. You don’t need legalese—just an email that says, ‘This is what we agreed to.”
🔗 Conclusion:
Complex litigation isn’t just about courtrooms—it's about strategy, emotion, and preparation. This episode offers a roadmap for business owners to protect themselves long before disputes arise.
Connect with Josi:
Website: https://www.markowitzherbold.com/Josephine-Josi-Kovacs LinkedIn: https://www.linkedin.com/in/josephine-kovacs/\
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-tap
Facebook: https://www.facebook.com/3Dinvesting/
X: https://x.com/BFG_LLC/

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Bonus: From Residential Sales to Commercial Real Estate Development Jan 27, 2026

Show notes

In this episode of Sterling Insights, guest host Tracy McCary sits down with Taner Neighbors, a commercial real estate broker and third-generation real estate professional. Together, they explore the transition from residential real estate to commercial development, sharing valuable insights and practical tips for listeners navigating this complex industry. Tanner draws from his extensive experience to discuss the challenges of starting during a market crash, the evolving demands of the commercial sector, and how to bring value as a trusted advisor, offering actionable advice for professionals looking to elevate their role in real estate.

This episode is a must-listen for advisors, brokers, and anyone eyeing a move into commercial real estate or development, providing both knowledge and tools to navigate this important subject.

Key Takeaways:

Start Where You Are: Launching a real estate career during the 2008 crash taught Tanner resilience, creativity, and long-term grit.
Residential vs. Commercial: Why Tanner moved away from residential sales and how commercial real estate offers deeper value and specialization.
The Power of Partnerships: How working with a seasoned developer has opened doors in capital raising and ground-up projects.
Market Impact of Interest Rates: Understanding how even small interest rate changes drastically shift commercial property valuations.
Become the Trusted Advisor: It’s not about being everywhere—it’s about evolving daily and being the expert people rely on.

Quotes from Taner Neighbors:

"I don't like selling houses—I enjoy the commercial side of things tremendously."
"Interest rates 100,000% drive the commercial real estate market."
"A true professional can make your life very easy. Time is something we can never get back."

🔗 Conclusion:

This episode highlights what it takes to move beyond transactional real estate into a role of influence, strategy, and long-term impact. Whether you're advising high-net-worth clients or building your own real estate career, Taner’s journey offers both inspiration and a roadmap forward.

Connect with Taner:

LinkedIn: https://www.linkedin.com/in/neighborssells/

Connect with Tracy:

Website: https://tracwealthmanagement.com/

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Bonus: Estate Planning for High-Net-Worth Families: Trusts, Taxes & Probate Tips Jan 22, 2026

Show notes

Think your estate plan is “simple”? Think again. This episode will make you rethink what it really takes to protect your family, your assets, and your legacy.
In this episode of Sterling Insights, guest host Peter Florio sits down with attorney and estate planning expert Robin Maynard, partner at Marquesian Mayer. Together, they explore the complexities of estate planning for high-net-worth families, sharing valuable insights and practical tips for listeners. Robin draws from her extensive experience to discuss common pitfalls, tax-saving strategies, and why proper trust planning is essential. This episode is a must-listen for financial advisors, wealth managers, and families with significant assets, providing both knowledge and tools to navigate this important subject.
Key Takeaways:
● Trusts Simplify—and Speed Up—the Estate Process: Avoid probate delays by ensuring assets are properly titled within a trust.
● Tax Law Is a Moving Target: Estate plans must include flexibility to adapt to evolving federal and state tax laws.
● Family Dynamics Can Complicate Estates: Proactive planning minimizes family conflict and emotional strain after a death.
● Everyone Thinks Their Estate Is “Simple”—Until It Isn’t: Even straightforward estates come with complexities most people overlook.
● Collaborating with Financial Advisors Is Critical: Integrated planning between legal and financial professionals leads to better outcomes for clients.
Quotes from Robin Maynard:
● “Every conversation starts with, ‘This is simple,’ and then it never is.”
● “People don’t realize their estate plan fails if their trust is empty.”
● “The bureau will take your money for tuition, but won’t give you a refund check without a power of attorney.”
🔗 Conclusion:
Estate planning isn’t just for the ultra-wealthy or the elderly—it’s for anyone who wants clarity, control, and peace of mind for the future. This episode lays out what smart planning looks like—and why it pays to get it right.

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Episode 49: Inside a $10B RIA: Scaling Pinnacle and Serving High Net Worth Clients Jan 21, 2026

Show notes

What does it take to scale a $10B RIA while staying true to a client-first culture? This episode explores the systems, people, and strategies behind sustainable growth in wealth management.

In this episode of Sterling Insights, Roger sits down with Scott Brown, President of Pinnacle Associates, a multibillion-dollar RIA serving high net worth families and institutions. Together, they explore what it takes to build and grow a thriving independent advisory firm, sharing valuable insights and practical tips for listeners. Scott draws from his extensive legal and operational experience to discuss the evolution of the RIA space, the importance of culture, and how firms can stay competitive in a fast-changing landscape. This episode is a must-listen for financial advisors, firm leaders, and professionals serving HNW clients, providing both knowledge and tools to navigate growth, succession, and innovation in wealth management.

🔑 Key Takeaways:

● Culture Drives Client Experience: Pinnacle prioritizes internal culture, believing happy, respected employees create the best outcomes for clients.

● Built to Scale: From in-house investment management to advisor training programs, Pinnacle is structured to grow without sacrificing quality.

● Focus on the $2M–$20M Client: Their ideal client range allows for deep planning relationships, with business owners and entrepreneurs being a core audience.

● Organic + Inorganic Growth Strategy: Pinnacle targets 5%+ organic growth while selectively pursuing M&A to expand strategically.

● Future-Proofing the RIA: With initiatives like the Next Gen Committee and Pinnacle Academy, they’re investing in leadership, tech, and talent to stay ahead.

💬 Quotes from Scott Brown:

● "We’re trying to build a firm that thinks three chess moves ahead — not just one client meeting at a time."

● "Culture is the number one thing we care about. Good people lead to great client experiences."

● "It’s a unique time in the RIA world — consolidation, AI, and client expectations are all shifting. You need to be paying attention."

🔗 Conclusion: If you're serious about growing a client-first advisory business that lasts, this episode delivers real-world strategies from the front lines of a $10B RIA.

Connect with Scott:

Website: https://www.pinnacle-associates.com

LinkedIn: https://www.linkedin.com/in/scottbrown1999/

LinkedIn: https://www.linkedin.com/company/pinnacle-associates/?viewAsMember=true

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/

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From Pro Athlete to CPA: Scaling Trades Businesses & High-Net-Worth Tax Strategy Jan 20, 2026

Show notes

What happens when a pro basketball player trades the court for cash flow consulting? This episode dives into how blue-collar businesses can build wealth with the right CPA on their team.
In this episode of Sterling Insights, guest host Tracy McCary sits down with Mark Stiles, CPA and founder of MAS CPA. Together, they explore the power of proactive accounting and fractional CFO services, especially for trades and service-based businesses. Mark draws from his unique journey—from professional athlete to CPA—to discuss the challenges business owners face when scaling, including job costing, tax strategy, and navigating debt. This episode is a must-listen for advisors, accountants, and business owners working with high-net-worth individuals or growing blue-collar companies, offering both insights and action steps to take control of financial outcomes.
Key Takeaways:

🛠️ Know Your Niche: Trades businesses between $500K–$5M in revenue are often under-served—and wildly profitable with the right financial structure.
💰 Job Costing = Hidden Cash Flow: Most tradespeople don’t track profitability per job, leading to money left on the table.
📊 From Compliance to Strategy: CPAs must evolve from number crunchers to storytellers who help owners make smarter decisions.
🧠 DIY Pitfalls Are Real: Self-filing taxes or doing your own books often leads to costly mistakes—smart business owners delegate.
🚀 Charge for Your Value: Professionals need to stop pricing hourly and start pricing based on outcomes and real value delivered.

“We’re not just pencil pushers. We’re storytellers—and that’s where the real value is.”
“If you’re not resonating with your client, then you’re not a fit—and the relationship won’t be fruitful.”
“Don’t penny-pinch on your professionals. That’s the lifeblood of your business.”

Quotes from Mark Stiles:
Connect with Mark:
Website: https://www.markstilescpa.com
LinkedIn: https://www.linkedin.com/company/mascpa/
Facebook: https://www.facebook.com/share/1AscCpnvMy/?mibextid=wwXIfr
Instagram: https://www.instagram.com/mascpa_?igsh=Z2ZkYzk3c3RueDlm&utm_source=qr

Podcast: https://open.spotify.com/show/1Xgh8G0ENtln59anAwZwFI?si=nr6-xh12R26JcV9lqBtcqQ&nd=1&dlsi=27d11b68be02409a
Connect with Tracy:
Website: https://tracwealthmanagement.com/
🔗 Conclusion:
This episode shows how CPAs can be growth engines—not just compliance officers—for trades and high-net-worth clients. With storytelling, strategy, and specialization, accounting becomes a superpower.

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Bonus: From Farm to FinPro: Holistic Accounting for Blue-Collar Clients Jan 15, 2026

Show notes

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-roos
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=100011447285280
🔗 Conclusion:
Whether you serve farmers, contractors, or financial advisors, delivering integrated, high-trust accounting services can transform your client relationships—and your business.

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Episode 48: Succession Planning for Financial Advisors: How to Build Value and Transition Clients Jan 14, 2026

Show notes

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/

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