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.
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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 before making decisions based on fear.
Key Takeaways:
● Respond to IRS Notices Quickly: Ignoring an IRS letter can cause taxpayers to miss important deadlines and lose valuable rights.
● Understand Your Settlement Options: Offers in compromise, penalty abatements, collection statutes, and bankruptcy may provide solutions depending on the circumstances.
● Beware of “Pennies on the Dollar” Claims: IRS tax settlements are possible, but aggressive advertising often makes these outcomes appear far more common than they are.
● Get Representation During an Audit: Business owners should consider having an experienced tax professional communicate with the IRS rather than handling an audit themselves.
● File Even If You Can’t Pay: Delaying a tax return because you cannot afford the balance can create additional penalties and make the problem more expensive.
Episode 51: Smarter Pricing for Financial Advisors
Thursday, September 10, 2026 • Duration 13:16
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, and positioning can help advisors structure fees more effectively.
Key Takeaways:
● Underpricing Can Undermine Value: RIAs often price based on what feels fair to them rather than what their expertise is worth to clients.
● Pricing Is Both Art and Science: Sustainable pricing requires understanding margins and profitability while accounting for how clients make decisions.
● Give Clients Meaningful Choices: Offering structured pricing options gives prospects reference points and can make decisions easier than presenting one price or too many choices.
● Positioning Shapes Perceived Value: How and where an advisory service is presented can significantly influence what clients believe that service is worth.
● Use Anchoring Strategically: Advisors can establish relevant comparison points that help clients evaluate the value of their advice and pricing.
Bonus: CPA Strategies for Taxes, AI & High-Growth Businesses
Thursday, September 3, 2026 • Duration 26:13
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 financial decisions are far easier to manage when business owners plan ahead instead of waiting until deadlines or problems arise.
● Communication Builds Better Outcomes: Strong CPA-client relationships depend on consistent communication, realistic expectations, and a willingness to address issues early.
● Regulated Industries Require Specialized Knowledge: Businesses in emerging and highly regulated markets need advisors who understand evolving rules and know how to prepare for additional scrutiny.
● Modern Accounting Goes Beyond Compliance: Business owners can gain more value from CPAs who help evaluate opportunities, solve problems, and support strategic decisions rather than simply prepare forms.
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 create tax obligations, why California's new SaaS tax rules are a major development, and how proactive planning can reduce risk, uncover savings, and protect business value during growth.
Key Takeaways:
● Physical and economic nexus create different tax obligations that every growing business should understand.
● Remote employees, third-party inventory, and e-commerce expansion can unexpectedly trigger multi-state tax exposure.
● California's new SaaS tax rules make it critical for software companies selling into the state to prepare before 2027.
● M&A due diligence frequently uncovers hidden state tax liabilities that can impact valuation and deal structure.
● Regular nexus reviews help companies avoid costly penalties while identifying potential tax savings and refund opportunities.
Bonus: Beyond the Will: Estate Planning Mistakes, Trust Strategies, Tax Planning & Family Legacy
Wednesday, June 24, 2026 • Duration 43:04
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 Krussman to discuss the most common estate planning mistakes, the importance of trusts and beneficiary coordination, planning for special needs family members, charitable giving strategies, business succession planning, and why collaboration between attorneys, financial advisors, and CPAs leads to better outcomes. She also shares practical guidance on keeping estate plans current and protecting loved ones from unnecessary taxes, delays, and complications.
Key Takeaways:
● Estate Planning Is More Than a Will: Effective planning starts with goals, strategy, and coordination across all assets and family circumstances.
● Review Your Plan Regularly: Major life events, tax law changes, and evolving family dynamics can quickly make an outdated plan ineffective.
● Trusts Can Solve Multiple Problems: Trusts can provide privacy, tax planning opportunities, asset protection, and support for beneficiaries with special needs.
● Business Succession Requires Early Planning: Owners who build businesses that can operate without them create more value and smoother transitions.
● Advisor Collaboration Matters: Coordinated planning between attorneys, financial advisors, and CPAs helps families avoid costly mistakes and achieve better outcomes.
Connect with Tammi:
Bonus: Crypto Tax Rules Every Investor Should Understand
Wednesday, June 3, 2026 • Duration 30:23
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 taxable events without realizing it, why many broker-issued crypto tax forms may be inaccurate, and how advisors and accountants can stay ahead as digital assets become more mainstream.
Key Takeaways:
● Crypto tax reporting is evolving quickly: New 1099-DA rules are creating confusion for investors, accountants, and advisors navigating digital asset compliance.
● Many crypto tax forms may be incomplete: Investors using multiple wallets or exchanges often receive inaccurate cost-basis reporting.
● Financial advisors need crypto visibility: Advisors increasingly need insight into digital asset holdings to manage full portfolio strategy and tax planning.
● Blockchain creates massive data complexity: Crypto transactions, staking rewards, liquidity pools, and yield strategies generate difficult-to-track tax events.
● Education remains the biggest hurdle: Many investors and professionals still underestimate the importance of understanding crypto tax obligations.
Bonus: Advanced Estate Planning for High Net Worth Families
Wednesday, May 13, 2026 • Duration 37:01
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 can dramatically improve outcomes. The conversation highlights practical strategies around trusts, gifting, tax mitigation, and family dynamics—while emphasizing that clarity, communication, and timing are what truly drive effective planning.
Key Takeaways:
● Know your assets: A complete, organized asset list is critical to ensure your estate plan actually works as intended.
● Titling matters: Even the best trust structure fails if assets aren’t properly aligned and funded.
● Plan before liquidity events: Early coordination helps avoid major tax consequences during sales or exits.
● Family dynamics drive strategy: Effective planning must account for relationships, roles, and communication.
● Start earlier than you think: Estate planning is most effective when treated as an ongoing, proactive process.
Bonus: Senior Real Estate Specialist on Trust & Downsizing
Wednesday, April 29, 2026 • Duration 29:47
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 better outcomes and stronger referral-driven growth.
● Serving the 55+ market: Senior transitions require empathy, coordination, and guidance beyond a typical real estate transaction.
● Acting as a trusted advisor: Providing honest advice, even when it slows a deal, builds long-term credibility and client confidence.
● Negotiation and teamwork matter: Collaborating with agents and managing expectations helps deals stay together.
● Specialization creates differentiation: Focusing on senior downsizing and transitions helps stand out in a crowded real estate market.
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-listen for taxpayers, advisors, and anyone concerned about IRS debt, providing both knowledge and tools to navigate this important subject.
Key Takeaways:
● Not All Tax Debt Is Accurate: Many IRS balances are overstated due to substitute returns—fixing filings can significantly reduce what’s owed.
● Cause, Cure, Compliance Framework: Understanding why the debt happened, how to resolve it, and how to stay compliant is key to long-term success.
● Multiple Resolution Options Exist: Payment plans, hardship status, and offers in compromise depend on financial analysis—not negotiation.
● IRS Mistakes Happen: Even large payments can be misapplied, leading to major penalties and long disputes.
● Beware of Tax Relief Scams: Many firms overpromise “pennies on the dollar” but fail to deliver real results.
Bonus: Strategic Tax Planning for Entrepreneurs
Thursday, March 26, 2026 • Duration 29:18
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 discuss common misconceptions about CPAs, the importance of proactive tax planning, and how business owners can better align their financial strategies with long-term goals, offering actionable advice for entrepreneurs, business owners, and high-income professionals. This episode is a must-listen for anyone looking to move beyond basic tax preparation and leverage financial strategy for growth, providing both knowledge and tools to navigate this important subject.
Key Takeaways:
● CPAs Are Strategic Advisors—Not Just Tax Preparers:
Many people misunderstand the role of a CPA. The real value lies in strategic planning, not just filling out forms.
● Annual Tax Planning Is the Minimum Standard:
Business owners should meet with their CPA at least once a year—ideally before year-end—to proactively reduce tax liability and adjust strategy.
PeterF. Florio, CFP, CLU, ChFC, CExP, CLTC is a well-respected financial educator, author, speaker and wealth, tax and financial planner. For nearly 40 years, his advice and expertise have been sought out by high net worth individuals and small business owners to manage their wealth and protect their families and businesses from life’s unforeseen pratfalls.
Peter regularly shares his knowledge of innovative ideas and concepts with CPA’s and attorneys. He serves the needs of over 500 clients located throughout the country with a concentration in the Long Island/New York City area.
Peter is the Founder and Managing Partner of The Florio Wealth Management Group, a financial planning and wealth management firm located in Westbury, NY. He is a lifelong resident of Baldwin, New York, a member of the Kiwanis Club of Baldwin and an active supporter of the Long Island Cystic Fibrosis Foundation.
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.
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.
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.
Whether your goal is lifestyle, monetization, or legacy, your financial strategy should reflect and support that vision.
● Ideal Clients Are Growth-Oriented and Engaged:
Entrepreneurs, strategic investors, side hustlers, and startups benefit most when they actively engage in the planning process.
● AI Is an Opportunity—Not a Replacement:
While AI can enhance efficiency, it cannot replace the strategic insight and personalized guidance of a skilled CPA.
Quotes from Jon Czerwinski:
● “If the only thing your CPA does is fill out a form, you don’t have a CPA.”
● “You hire a CPA for what’s between their ears—not the tax return they produce.”
● “Your life goals and your tax plan have to be in sync—otherwise, you’re working against yourself.”
The most successful business owners don’t treat their CPA as a once-a-year necessity—they treat them as a year-round strategic partner who helps guide smarter decisions, minimize risk, and maximize long-term success.
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