The Long Game

Ben Lake, a financial professional who advises high-net-worth households on liquidity and tax-efficient borrowing. He walks through sudden cash needs, when to sell taxable assets or RSUs, HELOCs versus cash-out refinancing, margin loans and pledged-asset lines, and the rising use of box spread loans for tax-savvy borrowing.

Tax expert Ryan Dolan shares essential tips for smooth tax prep! He emphasizes the importance of hiring a consistent tax team for accuracy and continuity. Ryan advises starting document organization early and using a dashboard to keep track of finances. He explains the common pitfalls like confusing balance payments with estimated payments. Plus, the benefits of extensions are discussed, especially for those awaiting certain documents. Get ready to take charge of your taxes and avoid last-minute stress!

In this discussion, Ben Lake, a Chartered Financial Analyst and Certified Financial Planner, shares insights on short-term cash planning. He emphasizes the importance of aligning your money with specific goals like buying a home or starting a business. Ben warns against the risks of chasing market returns with funds earmarked for near-term needs. They also explore the benefits of high-yield savings accounts, tax-efficient options like municipal funds, and the potential pitfalls of CDs and I-bonds, ensuring listeners are equipped to make informed decisions.

Ryan Dolan, a licensed tax professional and financial advisor specializing in strategies for business owners, shares crucial insights on Q4 estimated tax payments. He explains the importance of understanding 110% vs. 90% safe harbor rules to avoid penalties. Ryan discusses the significance of annualizing income for seasonal businesses and how it can improve cash flow. Listeners learn why overpaying slightly in Q4 might be more beneficial than scrambling come April, along with strategic uses of withholding and bonuses to prevent underpayment surprises.

Cody Garrett, a Certified Financial Planner and co-author of 'Tax Planning to and Through Early Retirement,' shares valuable insights on tax-efficient retirement planning. He emphasizes the importance of understanding income sources and timing Roth conversions strategically. Debunking misconceptions, Cody illustrates how tax deferral can outperform converting to Roth, even in potentially higher tax rate situations. With real-life examples, he advises on maximizing tax efficiency and stresses the need for personalized financial strategies, especially for entrepreneurs seeking liquidity.

Planning for a baby's arrival involves critical financial steps. Understanding the necessity of updating life insurance is vital for new parents. It’s essential to promptly add your newborn to your health insurance. Establishing an estate plan ensures your family's future is safeguarded. Reassessing your budget and emergency fund is key to managing new expenses. Utilizing a Dependent Care FSA can help save on childcare costs. Finally, exploring savings options for your child's future education is crucial.

In this discussion, Certified Financial Planner Mark Cecchini shares his journey of developing modern advisory practices. He emphasizes the importance of niching to avoid being pigeonholed and becoming a sought-after expert. Mark and Thomas explore the value of personal branding and social media in attracting clients, as well as the challenges of managing client relationships. They also touch on the significance of a tailored onboarding process and the need for transparency in demonstrating value to clients. Practical advice for aspiring advisors is provided throughout.

Wes Gray, a financial expert with years of experience living in Puerto Rico, shares invaluable insights on the benefits of relocating under Act 60. He breaks down the requirements for bona fide residency, revealing how to enjoy 0% capital gains on post-move earnings while navigating complex tax implications. Their discussion also covers lifestyle trade-offs, practical considerations for moving, and why the 4% export services tax might make sense for high earners. Wes emphasizes the importance of assessing personal situations before making such a significant shift.

Proactive tax planning is essential for avoiding penalties and maximizing savings. Discover strategies like optimizing 401(k) contributions and utilizing HSAs before year-end. Learn about tax loss harvesting to offset gains and the benefits of Roth conversions during low brackets. Explore the impact of charitable donations amid new AGI rules and how to review your business structure for tax advantages. Lastly, consider annual gifting to reduce estate size and ensure you're ready to capture every savings opportunity before the year closes.

Nate Sosa, a CPA with expertise in real estate taxation, joins to reveal powerful tax strategies for real estate investors. He breaks down the mechanics of depreciation and its significance in reducing taxable income. Sosa explains the distinctions between active and passive income, and how specific tax treatments can benefit high-income earners. The discussion also covers cost segregation, smart timing for bonus depreciation, and the unique tax implications of short-term rentals. Listeners can learn to navigate these strategies for maximum savings.