Business Insights

Market Domination
Market Domination

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.

  1. Jul 30 ·  Bonus

    Bonus: California's New SaaS Tax Law Explained

    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 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: seth@brayshawfinancial.com Website: brayshawfinancial.com Podcast: https://www.brayshawfinancial.com/money-on-tap Facebook: https://www.facebook.com/3Dinvesting/ Twitter: https://x.com/BFG_LLC/

    Bonus: California's New SaaS Tax Law Explained

  2. Jun 24 ·  Bonus

    Bonus: Beyond the Will: Estate Planning Mistakes, Trust Strategies, Tax Planning & Family Legacy

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

    Bonus: Beyond the Will: Estate Planning Mistakes, Trust Strategies, Tax Planning & Family Legacy

  3. Jun 3 ·  Bonus

    Bonus: Crypto Tax Rules Every Investor Should Understand

    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: Crypto Tax Rules Every Investor Should Understand

  4. May 13 ·  Bonus

    Bonus: Advanced Estate Planning for High Net Worth Families

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

  5. Apr 29 ·  Bonus

    Bonus: Senior Real Estate Specialist on Trust & Downsizing

    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.com Connect with Mike Agol: Website:  https://www.ridgecapitalmanagement.com/

    Bonus: Senior Real Estate Specialist on Trust & Downsizing

  6. Apr 2 ·  Bonus

    Bonus: IRS Insider on Fixing Back Taxes

    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/

    Bonus: IRS Insider on Fixing Back Taxes

  7. Mar 26

    Bonus: Strategic Tax Planning for Entrepreneurs

    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

    Bonus: Strategic Tax Planning for Entrepreneurs

  8. Mar 18 ·  Bonus

    Bonus: Tax Planning Strategies for Business Owners

    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.

    Bonus: Tax Planning Strategies for Business Owners
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Ratings & Reviews

5
out of 5
96 Ratings

About

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.

Information

  • Channel
    Market Domination
  • Creator
    Seth Greene
  • Years Active
    2024 - 2026
  • Episodes
    105
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Business Insights. Seth Greene. All Right Reserved.

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