Business Insights

International Tax Planning to Avoid Costly Cross-Border Mistakes

Evgenia (Eve) Belyavskaya, Tax Partner in the International Tax Specialty Group at PKF O'Connor Davies, brings more than 15 years of experience advising businesses, executives, and high-net-worth individuals on international tax matters.

In this episode, guest host Peter Florio explores the complexities of cross-border tax planning, from expanding businesses internationally to relocating overseas. Eve shares common tax mistakes, overlooked compliance requirements, and why proactive planning is essential to protecting wealth, minimizing risk, and navigating international opportunities.

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How to Cut Business Technology Costs and Avoid Costly IT Mistakes | Blake Patterson

Blake Patterson, founder and president of Exploring IT Solutions, joins Seth Krussman on the Business Insights podcast to share insights from more than a decade working with major technology and telecommunications providers, including Comcast, Verizon, and T-Mobile.

From hidden IT expenses and restrictive vendor contracts to cybersecurity, AI, and technology planning, Blake explains how business owners can make smarter technology decisions, reduce unnecessary costs, and avoid common purchasing mistakes. Discover why comparing providers, standardizing technology across...

Mike Milligan is the founder of OneOak Financial, an author, financial strategist, and entrepreneur who has built an Inc. 5000 company with a 30-plus-person team serving clients across the United States. His approach to financial planning emphasizes tax strategy alongside investments and retirement planning.

In this episode, Mike shares how his early experiences with money shaped his career, why taxes can be one of the biggest expenses in retirement, and how better planning can help individuals and business owners keep more of what they earn. He also explores advisor fees, Roth conversions, required minimum distributions...

Estate planning is about more than documents—it’s about making sure your assets, advisors, and intentions actually work together.

Chris Carns is a board-certified estate planning and probate attorney and partner at Hessie, Blythe & Carns in Plano, Texas, with roughly 15 years of experience serving families, business owners, and high-net-worth clients. In this episode, Chris breaks down common estate planning mistakes, planning considerations for blended families and business owners, and why coordination among attorneys, CPAs, and financial advisors becomes increasingly important as wealth grows.

Key Takeaways:

Joshua Kreitzman, CPA and owner of Kreitzman & Company, brings more than 20 years of experience spanning financial management, nonprofit leadership, entertainment production, and business advisory work. His firm serves hundreds of businesses and individuals, with particular experience working with contractors, construction companies, and family-owned businesses.

In this episode, Joshua joins guest host Peter Florio to discuss his unconventional journey from theater to accounting and how skills like active listening, communication, and collaboration shape his approach to advising business owners. They also explore the changing accounting profession, the impact of AI and virtual...

Marcelino Dodge is an Enrolled Agent, Certified Tax Representation Consultant, and founder of Cash Tracks Financial and Panther Tax Resolution, helping individuals and business owners resolve tax problems and plan more effectively.

In this episode, Marcelino breaks down common tax mistakes, from choosing the wrong business structure and relying on questionable tax advice to mishandling retirement withdrawals and waiting too long to address IRS problems. He also explains how tax resolution works, why planning ahead matters, and how tax and investment professionals can work together to help clients make better-informed financial decisions.

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Jason Wiggam is the founding partner of Wiggam Law, an Atlanta-based tax controversy firm representing individuals, business owners, executives, and investors in disputes with the IRS and state tax authorities. His firm serves clients nationwide and has grown from a two-person operation to a team of 50.

In this episode, Jason explains what business owners should know when facing IRS audits, tax debt, collection notices, and settlement options. He breaks down common misconceptions about the IRS, why ignoring notices can be costly, how offers in compromise really work, and why taxpayers should understand their options...

Armine Alajian is a CPA, entrepreneur, and founder and CEO of the Alajian Group, a full-service accounting and advisory firm serving startups, growing businesses, entrepreneurs, and high-net-worth individuals. With more than 20 years of experience spanning public accounting, corporate finance, fintech, tax strategy, and fractional CFO services, she helps business owners turn financial data into better decisions.

In this episode, Armine joins guest host Peter Florio to explain why accounting should go far beyond preparing tax returns. They discuss the importance of accurate financial reporting, cash flow management, fractional CFO support, AI and automation, and...

Behavioral economics may be the missing piece in how RIAs price and position their advice.

Etinosa Agbonlahor is a behavioral economist and CEO of Decision Alpha, where she applies behavioral economics to pricing, decision-making, product design, and growth. Her experience includes working with major banks in Australia and a large U.S. investment firm.

In this episode, Etinosa explores why RIAs and business owners often underprice their services, how clients perceive value, and why pricing requires both math and psychology. She also explains how anchoring, pricing options, client segmentation...

For businesses in fast-changing industries, the right CPA can be more than a tax preparer—they can become an essential part of the team.

Zachary Gordon, CPA, founder of Red Five Services, brings experience across public accounting, private equity, startups, and highly regulated industries including cannabis and technology. In this episode, Zach shares how proactive planning, clear communication, modern accounting practices, and a true advisory relationship can help business owners navigate complex regulations, manage growth, and make better financial decisions.

Key Takeaways:

● Proactive Planning Matters: Tax and fina...

California's New SaaS Tax Law Explained

State tax rules can quietly become one of the biggest risks facing growing businesses.

Penny Sweeting is a Senior Tax Manager at Withum specializing in state and local tax (SALT), nexus, and multi-state expansion. She helps businesses identify tax exposure before it becomes an expensive compliance problem, particularly as companies grow across state lines, hire remote employees, or prepare for mergers and acquisitions.

In this episode, Penny explains what tax nexus really means, how economic and physical presence...

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 business succession, she helps families and business owners navigate complex estate planning decisions with clarity and confidence.

In this episode, Tammi joins Seth K...

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 crypto taxes, 1099-DA reporting, digital asset compliance, and how financial advisors can better manage crypto within client portfolios.

He also explains how crypto investors create ta...

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 episode, Natalie breaks down what “advanced” estate planning actually means, where high net worth families and business owners make costly mistakes, and how early coordination with advisors c...

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 service and integrity separate advisors from transactional agents.

Key Takeaways:

● Relationship-first real estate: Building trust and personal connections leads to bett...

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 former IRS revenue officer to discuss how tax debt is calculated, resolved, and sometimes reduced, offering actionable advice for individuals and business owners dealing with IRS issues. This episode is a must-l...

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 evolving role of CPAs as strategic partners in business growth, sharing valuable insights and practical tips for listeners. Jon draws from his extensive experience to disc...

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 for business owners and retirees, sharing valuable insights and practical strategies that go far beyond basic tax preparation. Dana draws from his extensive experience in public accounting and as a former contro...

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 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...

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 nav...

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 nav...

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 RI...

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 RI...

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 listener...

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 listener...

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 dis...

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 dis...

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...

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...

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...

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...

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...

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...

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 ac...

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 ac...

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.

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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.

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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 man...

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 man...

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...