Business Insights

Episoder

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  Bonus: From Actor to CPA: Smarter Financial Decisions for Business Owners 08.10.2026 35min

  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 work, and why strong professional relationships go far beyond preparing tax returns.Key Takeaways:● Listening Is a Business Skill: Joshua explains how his theater background taught him to listen closely, understand what clients really need, and communicate financial information more effectively.● Keep Financial Decisions Simple: Breaking complex financial concepts into understandable terms helps business owners make more informed decisions and avoid unnecessary confusion.● Collaboration Creates Better Outcomes: Accountants, financial advisors, insurance professionals, and other specialists can provide greater value when they work together around the client.● Technology Is Changing Accounting: Virtual meetings, cloud-based tools, and AI are helping smaller accounting firms become more efficient and access sophisticated research capabilities.● Great Advisors Go Beyond Transactions: Building trust, understanding a client's goals, and supporting long-term growth can turn an accountant into a true business advisor.Connect with Josh:Website: www.kreitzmancpas.comWith Guest Host Peter Florio:Peter F. 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.  Website: https://www.floriowmg.comLinkedIn: https://www.linkedin.com/company/florio-wealth-management-group/Facebook: https://www.facebook.com/floriowmgCalendly: https://calendly.com/floriowmg
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  Bonus: IRS Tax Problems: Resolve Tax Debt & Avoid Costly Mistakes 01.10.2026 49min

  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.Key Takeaways:● Choose the Right Business Structure: The wrong entity or tax election can lead business owners to pay more in taxes than necessary.● Plan Before Major Financial Moves: Retirement withdrawals, business decisions, and other significant transactions can create unexpected tax consequences without advance planning.● Understand Tax Resolution: Offers in compromise, installment agreements, and other IRS solutions have specific qualification requirements and are not automatic.● Stay Current With the IRS: Filing required tax returns and maintaining compliance can be critical when trying to resolve an existing tax problem.● Coordinate Financial and Tax Planning: Collaboration between tax and investment professionals can help clients anticipate tax consequences andConnect with Marcelino:Website: www.taxreliefcall.comWebsite: www.cashtracksfinancial.comCalendly: Select a Date & Time - CalendlyFacebook: https://www.facebook.com/CashTracksCOS/YouTube: https://youtube.com/channel/UC9HIcpd8lTskcc2lwlGPZMAWith your Guest Host Dana Gibson:Dana Gibson is a Retirement Diagnostician and Certified Financial Fiduciary known as The Roth Doctor™. His approach was shaped by a life-changing 1995 assault and subsequent financial devastation, which taught him how quickly health, wealth, and financial security can change.Today, Dana helps pre-retirees identify hidden risks involving taxes, RMDs, Social Security, retirement income, longevity, and wealth preservation. He also developed the Self-Completing Roth Conversion Strategy to help families reduce lifetime retirement taxes.Dana’s philosophy is simple: every retirement deserves a thorough diagnosis before a financial prescription.Website: https://taxmitigation.net/tax-readiness-score.html
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  Episode 52: IRS Tax Problems: Audits, Tax Debt & Settlements 24.09.2026 15min

  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.Connect with Jason:LinkedIn:  https://www.linkedin.com/in/jasonwiggam/Website:  https://wiggamlaw.com
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  Bonus: Beyond Taxes: Accounting & Cash Flow for Business Growth 17.09.2026 21min

  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 building the financial infrastructure businesses need to grow, raise capital, and prepare for future opportunities.Key Takeaways:● Accounting Goes Beyond Taxes: Strong accounting gives business owners the financial information they need to make informed decisions throughout the year.● Cash Flow Is Critical: Understanding when money actually comes in and goes out helps businesses anticipate needs and avoid costly surprises.● Financial Infrastructure Supports Growth: Reliable reporting, internal controls, and clean financial data become increasingly important as a company scales.● Fractional CFOs Fill a Strategic Gap: Growing businesses can access projections, analytics, fundraising support, and higher-level financial guidance without building a full internal finance department.● AI Is a Tool, Not a Replacement: AI and automation can make accounting more efficient, but professional expertise remains essential for evaluating information and applying it correctly.Connect with Armine:Website:  www.alajiangroup.comWith Guest Host Peter Florio:Peter F. 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.  Website: https://www.floriowmg.comLinkedIn: https://www.linkedin.com/company/florio-wealth-management-group/Facebook: https://www.facebook.com/floriowmgCalendly: https://calendly.com/floriowmg
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  Episode 51: Smarter Pricing for Financial Advisors 10.09.2026 13min

  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.Connect with Etinosa:Website: www.etinosaa.com
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  Bonus: CPA Strategies for Taxes, AI & High-Growth Businesses 03.09.2026 26min

  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.Connect with Zachary:LinkedIn: https://www.linkedin.com/in/zacharygordon-cpa/Website: https://redfiveservices.com/With your Guest Host Peter Florio:Peter F. 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.  Website: https://www.floriowmg.comLinkedIn: https://www.linkedin.com/company/florio-wealth-management-group/Facebook: https://www.facebook.com/floriowmgCalendly: https://calendly.com/floriowmg
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  Bonus: California's New SaaS Tax Law Explained 30.07.2026 43min

  California's New SaaS Tax Law ExplainedState 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.Connect with Penny:Website: https://www.withum.com/service/tax/state-and-local-tax/Website: https://www.withum.com/state-and-local-tax-updates/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.Email: [email protected]: brayshawfinancial.comPodcast: https://www.brayshawfinancial.com/money-on-tapFacebook: https://www.facebook.com/3Dinvesting/Twitter: https://x.com/BFG_LLC/
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  Bonus: Beyond the Will: Estate Planning Mistakes, Trust Strategies, Tax Planning & Family Legacy 24.06.2026 43min

  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:Website: https://caresslaw.estateLinkedIn: https://www.linkedin.com/company/caress-law/Instagram: https://www.instagram.com/caresslaw/Facebook: https://www.facebook.com/caresslaw.estate/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-tapFacebook: https://www.facebook.com/3Dinvesting/X: https://x.com/BFG_LLC/
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  Bonus: Crypto Tax Rules Every Investor Should Understand 03.06.2026 30min

  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.
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  Bonus: Advanced Estate Planning for High Net Worth Families 13.05.2026 37min

  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.Connect with Natalie:Website: https://www.sussmanshank.com/people/natalie-e-smith-ll-m/LinkedIn: https://www.linkedin.com/in/natalieelizabethsmith/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-tapFacebook: https://www.facebook.com/3Dinvesting/X: https://x.com/BFG_LLC/
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  Bonus: Senior Real Estate Specialist on Trust & Downsizing 29.04.2026 29min

  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.Connect with Leroy:Website:  https://www.silvershoresrealty.comConnect with Mike Agol:Website:  https://www.ridgecapitalmanagement.com/
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  Bonus: IRS Insider on Fixing Back Taxes 02.04.2026 33min

  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.Quotes from Michael Raanan:● “It’s not that big of a deal when you owe back taxes—you just have to address it.”● “The IRS is very black and white. It’s about what you qualify for, not negotiation.”● “We hear it all the time—‘they didn’t do anything for me’—that’s the reality with a lot of these tax relief firms.”Understanding how the IRS actually works—and what options truly exist—can turn a stressful tax problem into a manageable plan forward.Connect with Michael:Website:  https://landmarktaxgroup.com/
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  Bonus: Strategic Tax Planning for Entrepreneurs 26.03.2026 29min

  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.● Your Tax Plan Must Align With Your Life Goals: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.Connect with Jon:Website - https://www.jccpas.com/Instagram - https://instagram.com/jccpas/LinkedIn - https://linkedin.com/company/jccpas/about/Facebook - https://www.facebook.com/profile.php?id=61561069991961
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  Bonus: Tax Planning Strategies for Business Owners 18.03.2026 20min

  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 controller to discuss Roth conversions, IRMAA planning, 1099 estimated tax mistakes, succession planning, and smart exit strategies—offering actionable advice for business owners, independent contractors, and retirees.This episode is a must-listen for entrepreneurs, construction and restaurant owners, and high-income professionals who want to reduce taxes, avoid costly surprises, and build a smarter long-term financial strategy.Key Takeaways:● Proactive Tax Planning Beats Reactive Tax Filing: Tax preparation is compliance — tax planning is strategy. Business owners who plan ahead can significantly reduce lifetime tax liability.● Roth Conversions & IRMAA Awareness Matter in Retirement: Strategic Roth conversions can reduce required minimum distributions (RMDs) and prevent costly Medicare premium increases tied to income thresholds.● 1099 Income Requires Quarterly Payments: Independent contractors must make estimated tax payments to avoid penalties and painful April surprises.● Exit & Succession Planning Has Major Tax Implications: Selling, expanding, or transitioning a business requires careful asset allocation and coordination with advisors to minimize tax impact.● Staffing Is the Biggest Challenge in Accounting Today: With hundreds of thousands of CPAs exiting the profession, access to responsive, relationship-driven advisory services is becoming increasingly valuable.Quotes from Dana Lashbaugh:● “We’re not just preparing tax returns — we’re helping clients plan where they’re going.”● “There’s really no such thing as a quick tax question — because the right answer depends on the details.”● “The pain is a lot easier quarterly than getting one big surprise bill on April 15th.”Smart tax planning isn’t about being aggressive — it’s about being intentional. The earlier business owners and retirees plan, the more control they maintain over taxes, cash flow, and long-term wealth.
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  Episode 50: Tax-Efficient Strategies for Concentrated Stock & Roth Conversions 11.03.2026 26min

  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-listen for high-net-worth individuals and financial professionals seeking smarter, more integrated planning strategies.Key Takeaways:● Concentration Risk Starts Around 10%: While 10% in a single stock is a common rule of thumb, true risk tolerance depends on age, goals, income sources, and overall net worth.● Create a Rules-Based Liquidation Strategy: Removing emotion from selling appreciated stock by setting pre-defined triggers can help investors diversify systematically and tax-efficiently.● Roth Conversions Require Careful Modeling: Conversions can increase lifetime wealth—but hidden “tax torpedoes” like Social Security taxation, capital gains brackets, and Medicare premiums must be considered.● Integrate Tax, Estate, and Investment Planning: The most effective strategies align tax efficiency, legacy intent, and portfolio design into one coordinated plan.● Advanced Tools Improve Planning Outcomes: Modern tax and financial planning software allows advisors to model “what-if” scenarios efficiently, enabling dynamic, data-driven decisions.Quotes from Gary Pattengale:● “Taxes are important—but first we assess the concentration risk. What happens if that stock drops 40 to 60%?”● “Once the rule is triggered, we execute. It takes the emotion out of it.”● “Roth conversions aren’t for everybody. You really have to analyze the full tax impact before you act.”True wealth management isn’t about chasing returns—it’s about integrating tax strategy, risk management, and long-term planning into one cohesive approach that protects and grows wealth across generations.Connect with Gary:Website:  https://www.mesirow.com/homeLinkedIn:  https://www.linkedin.com/in/gary-pattengale-cfp%C2%AE-3806b822/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/ Learn more about your ad choices. Visit megaphone.fm/adchoices
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  Bonus: League City Insurance Agency Home Auto Life Umbrella Farmers Insurance 05.03.2026 16min

  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 navigate this critical subject. Key Takeaways: ● Value Over Price: The cheapest policy is rarely the best policy. Proper coverage protects everything you’ve worked hard to build. ● Umbrella Policies Matter: An umbrella policy is one of the most affordable ways to shield assets from major lawsuits and liability claims. ● Coverage Gaps Are Common: Jewelry, small business exposures, and liability risks are often underinsured or misunderstood. ● Advisors Should Collaborate: Insurance and financial advisors must work together to fully protect a client’s portfolio. ● Insurance Is Personal: True service goes beyond policies — it means showing up during freezes, hurricanes, and life’s toughest moments. Quotes from Angie Smith: ● “On a bad day, I want to make sure what you’ve built is still protected.” ● “An umbrella policy is the cheapest attorney you’ll ever have protecting your assets.” ● “We don’t just sell a policy — we sell value and proper protection.” Building wealth is only half the equation — protecting it is what secures your legacy. Learn more about your ad choices. Visit megaphone.fm/adchoices
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  Fan Fav: Centered Leadership in Wealth Management 25.02.2026 25min

  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 RIAs are reshaping wealth advisory. This episode is a must-listen for ultra-high-net-worth families, founders approaching liquidity, and professionals building modern client-first financial firms, providing both knowledge and tools to navigate this important subject. Key Takeaways:● 💼 Client-First DNA: Crescent’s model was literally built by clients, for clients, offering flexibility that traditional banks can’t match.● 🏛️ RIAs vs. Banks: Regulatory constraints limit the services banks can provide—RIAs like Crescent offer broader, deeper support in tax and private investing.● 🔍 Fit Over Size: Crescent’s ideal client isn’t just about net worth—it’s about mindset and the desire for holistic, customizable support.● 🧑‍🤝‍🧑 Team Culture Drives Client Success: Exceptional service starts with exceptional culture—Crescent prioritizes servant leaders and long interview processes to build elite teams.● 📈 Scale Matters—for the Right Reasons: Being “industrial-grade” at $50B+ AUM allows for better infrastructure, tech, and access—without losing the boutique client feel. Quotes from Susie Cranston:● “Our origin story is unique—we were built by clients, for clients.”● “You can’t outsource culture. It’s the best predictor of organizational success.”● “We aim to be the co-pilot in a family's financial life—scaling with them across the journey.” 🔗 Crescent offers what most firms can’t: customized service backed by enterprise-level infrastructure. Learn more at crescentcapital.com and tune into this episode to see what the future of wealth management looks like. Learn more about your ad choices. Visit megaphone.fm/adchoices
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  Bonus: Tax Strategy, IRS Relief, and Building a Virtual CPA Firm 12.02.2026 19min

  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 listeners. Adam draws from his 28+ years of experience to discuss how to effectively handle tax debt, avoid costly mistakes, and optimize taxes for high earners, offering actionable advice for wealth advisors, business owners, and high-income individuals. This episode is a must-listen for advisors with high-net-worth clients or anyone seeking smarter, proactive ways to tackle tax complexity.Key Takeaways:● Tax Resolution is More Than Numbers: Addressing tax debt isn’t just financial—it can dramatically improve a client’s mindset, health, and quality of life.● Don't DIY the IRS: Trying to resolve issues with the IRS yourself can backfire. Adam explains why professional representation matters.● Virtual Firms Are Winning: Adam shares how his remote model helps him recruit top talent and serve clients nationwide without geographic limitations.● Tax Misconceptions Hurt Clients: Many people unknowingly overpay or misreport—leading to years of unnecessary stress or tax court battles.● Advanced Strategies for High Earners: Adam reveals how clients earning $400k+ can use overlooked strategies to reduce income and capital gains taxes.Quotes from Adam Remis:● "Helping clients resolve their IRS debt isn’t just about money—it’s about lifting a massive psychological burden."● "Doing it yourself with the IRS is like representing yourself in criminal court. You need an expert in your corner."● "The details matter. We’ve saved clients tens of thousands simply by doing the digging their previous CPAs didn’t."Whether you're an advisor looking to better support high-net-worth clients or someone navigating complex tax issues yourself, this episode offers a rare behind-the-scenes look at how smart strategy—and the right partner—can make all the difference.Connect with Adam:Website:  https://www.theaccountingdoctor.comLinkedIn:  https://www.linkedin.com/in/adam-b-remis-msim-cpa-l-i-o-n-b354b1/ Learn more about your ad choices. Visit megaphone.fm/adchoices
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  Bonus: Understanding Employment Law: Workplace Rights & Wrongful Termination 10.02.2026 27min

  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 discuss wrongful termination, wage and hour disputes, discrimination claims, and the misconceptions employees often have about their rights, offering actionable advice for anyone navigating workplace challenges. This episode is a must-listen for professionals, business owners, HR managers, and employees facing tough job transitions, providing both knowledge and tools to understand and protect your rights.Key Takeaways:● The Harsh Truth About Employment at Will: Most private-sector employees can be terminated for any reason—or no reason at all—unless specific legal protections apply.● Unfair ≠ Illegal: Many workplace terminations may feel unfair but don't meet the legal threshold for wrongful termination or discrimination.● Wage & Hour Laws Are a Legal Minefield for Employers: Employers often violate wage laws without realizing it—missing notices, misclassifying employees, or improperly calculating overtime.● Discrimination Protections Exist—but Proof Is Key: Laws protect against discrimination based on race, gender, age, and more, but proving it can be difficult and requires strong documentation.● Legal Action Isn’t the Only Path: Sometimes, a well-crafted letter or negotiation can resolve disputes without litigation, especially when handled by an experienced advocate.Quotes from Raymond Nardo:● "Law and justice are distant cousins when it comes to employment law."● "Nine out of ten people who call me don’t have a case—because employment at will gives employers broad leeway."● "Even if we don’t win a case, we raise awareness—and that can change how employers operate going forward."🔗 Conclusion:Whether you’re an employee wondering if your termination was legal, or an employer navigating compliance, understanding the realities of employment law is critical. This episode sheds light on the rights, risks, and real-world processes behind workplace disputes.Connect with Raymond: Website:  https://www.raynardo.com/With Your Guest Host Peter Florio:Peter F. Florio, CFP®, CLU®, ChFC®, CExP™, CLTC®, is the Founder and Managing Partner of The Florio Wealth Management Group in Westbury, NY. With nearly 40 years of experience, he provides comprehensive wealth, tax, and financial planning for high-net-worth individuals and business owners across the country.Connect with Peter:Website: https://www.floriowmg.comLinkedIn: https://www.linkedin.com/company/florio-wealth-management-group/Facebook: https://www.facebook.com/floriowmgCalendly: https://calendly.com/floriowmg Learn more about your ad choices. Visit megaphone.fm/adchoices
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  Bonus: How Proactive Legal Strategy Protects Growing Businesses 05.02.2026 1t 3min

  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-tapFacebook:  https://www.facebook.com/3Dinvesting/X:  https://x.com/BFG_LLC/ Learn more about your ad choices. Visit megaphone.fm/adchoices