Bonus: Senior Real Estate Specialist on Trust & Downsizing

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 ● Review Your Plan Regularly: Major life events, tax law changes, and evolving family dynamics can quickly make an outdated plan ineffective.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 [https://caresslaw.estate/] LinkedIn: https://www.linkedin.com/company/caress-law [https://www.linkedin.com/company/caress-law/posts/?feedView=all]/ Instagram: https://www.instagram.com/caresslaw/ [https://www.instagram.com/caresslaw/] Facebook: https://www.facebook.com/caresslaw.estate/ [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/ [https://www.brayshawfinancial.com/] Podcast: https://www.brayshawfinancial.com/money-on-tap [https://www.brayshawfinancial.com/money-on-tap] Facebook: https://www.facebook.com/3Dinvesting/ [https://www.facebook.com/3Dinvesting/] X: https://x.com/BFG_LLC/ [https://x.com/BFG_LLC/]

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/]