Business Insights

Estate planning isn’t just about documents—it’s about protecting your family, your assets, and the legacy you leave behind. Tammi Caress is the founder and principal attorney of Caress Law in Portland, Oregon, and one of the few trust and estate attorneys in the Pacific Northwest to hold an LL.M. in Estate Planning. With decades of experience in probate, trust administration, tax planning, and bus...

Crypto taxes are getting more complicated fast — especially for investors, accountants, and financial advisors trying to keep up with new IRS reporting rules. Perry Woodin is the CEO and co-founder of Node40 , a digital asset accounting and analytics platform focused on crypto tax reporting, compliance, and financial reconciliation. In this episode, Perry breaks down the growing challenges around...

Estate planning isn’t just legal—it’s strategic, personal, and often misunderstood. Natalie Smith, attorney at Sussman Shank LLP, specializes in advanced estate, trust, and tax planning for families, business owners, and advisors. With an LLM and deep experience at the intersection of tax law and real-world decision-making, she helps clients align wealth, values, and long-term intent. In this epis...

Helping seniors navigate one of life’s biggest transitions requires trust, empathy, and a true relationship-first approach. Leroy Nashke, real estate agent with Silver Shores Realty and a Senior Real Estate Specialist, shares how he helps 55+ clients downsize, transition, and make confident decisions. He discusses building trust, coordinating services, avoiding costly mistakes, and why personal se...

What really happens when you owe the IRS—and how much of it is actually fixable? In this episode of Sterling Insights,  Tracy McCary  sits down with  Michael Raanan, Enrolled Agent and President of Landmark Tax Group . Together, they explore  IRS back taxes and tax resolution , sharing valuable insights and practical tips for listeners. Michael draws from his experience as a fo...

What if your CPA could do far more than file taxes—and actually help you build wealth, avoid costly mistakes, and align your finances with your life goals? In this episode of Sterling Insights , Mike Agol sits down with  Jon Czerwinski, CPA and Managing Partner , a strategic tax advisor specializing in entrepreneurs, investors, and high-growth businesses. Together, they explore  the evol...

Are you leaving money on the table because of poor tax planning — or worse, setting yourself up for an unexpected Medicare or IRS surprise? In this episode of  Sterling Insights , Tracy McCary sits down with  Dana Lashbaugh, CPA and Owner of The CPA Group , a tax strategist specializing in business owners earning between $2M–$20M in revenue. Together, they explore proactive tax planning...

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 Mesirow Wealth Management . Together, they explore tax-efficient strategies for managing concentrated stock positions, Roth conv...

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...

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 pract...

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 , C...

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 ,...

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...

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...

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 i...

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 va...

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 exper...

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 f...

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 wha...

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, esp...

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. Togethe...

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 ...

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  in...

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  advance...

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, s...