Bonus: Crypto Tax Rules Every Investor Should Understand

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 [https://node40.com/?utm_source=chatgpt.com], 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

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/

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

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/ [https://landmarktaxgroup.com/]

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/ [https://www.jccpas.com/] Instagram - https://instagram.com/jccpas/ [https://instagram.com/jccpas/] LinkedIn - https://linkedin.com/company/jccpas/about/ [https://linkedin.com/company/jccpas/about/] Facebook - https://www.facebook.com/profile.php?id=61561069991961 [https://www.facebook.com/profile.php?id=61561069991961]