The Long Game

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.

Join Colin Stroud, founder of Go Somewhere, as he unpacks the art of maximizing credit card points for savvy travelers. Colin shares why responsible credit card use can be a game-changer for wealthier consumers. He details the advantages of travel rewards versus cashback cards and introduces a simple two-card system for optimal earnings. Listeners will learn smart redemption strategies, the pitfalls of booking through card portals, and why starting with travel goals is crucial. If you want to travel smarter, this conversation is packed with invaluable insights!

In this episode, I break down the importance of understanding your pay stub. Many people overlook it, which can lead to missed tax opportunities, under-saving for retirement, and overpaying for benefits. Some highlights:Gross Pay: Understanding your full earnings before deductionsPre-Tax Deductions: How these can lower your taxable income and what to look forTaxes Withheld: Knowing your federal and state tax withholdingsAfter-Tax Deductions: Mega Backdoor Roth 401k and ESPPEmployer Benefits: What to track and consider for your overall compensationNet Pay: Knowing what you actually take home------✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

In this episode, I'm joined by Zach Ashburn to discuss the intersection of financial planning and personal freedom. Some highlights:The journey from corporate life to entrepreneurshipHow effective financial planning can empower you to make life-changing decisionsThe importance of liquidity and cash flow in achieving your ideal lifestyleReal-life stories of how financial planning has transformed lives (including Zach's experience as a foster parent and the impact it had on his family's decisions)How to maintain flexibility in your financial life----✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.