Maximize Your Roth: How to Decide the Right Conversion Amount

Subscribe to Cup of Bull: In this episode of Cup of Bull, Patrick Fontana and Michael Dunham discuss the concept of Roth conversions, emphasizing the importance of strategic tax planning for retirement. They explain how individuals can benefit from converting pre-tax retirement accounts to Roth accounts, particularly around specific life events or income fluctuations. The […]
Retire Well: The Power of a Comprehensive Financial Plan

Subscribe to Cup of Bull: In this episode of Cup of Bull, Patrick Fontana and Michael Dunham discuss the importance of financial independence over traditional retirement, emphasizing the need for a solid financial plan that provides peace of mind. They highlight common mistakes people make as they approach retirement, such as focusing too much on […]
Sell or Rent Your Home?

Are you planning a move and torn between selling or renting out your current home? In this video, we break down the key factors you need to consider — from financial implications and tax considerations to long-term goals. Whether you’re upgrading, downsizing, or relocating for work, making the right decision can have a major impact […]
The Biggest Tax Mistake Early Retirees Make

Subscribe to Cup of Bull! In this episode of Cup of Bull, Patrick Fontana and Michael Dunham discuss the critical tax mistakes individuals make as they enter retirement. They emphasizes the importance of understanding the retirement tax planning window, where individuals can take advantage of lower tax brackets before required minimum distributions kick in. Key […]
Strategies to Give to Charity in 2025

Subscribe to Cup of Bull! In this episode of Cup of Bull, Patrick Fontana and Michael Dunham discuss various strategies for charitable giving, focusing on maximizing tax benefits. They explain the importance of understanding individual circumstances, such as age and income, when planning charitable contributions. Key strategies include utilizing qualified charitable distributions (QCDs), the bunching […]
Should I Make Roth Retirement Contributions?

Subscribe to Cup of Bull! In this episode of Cup of Bull, Patrick Fontana and Michael Dunham discuss the advantages of Roth accounts, emphasizing their tax-free growth potential and strategic importance in financial planning. They explain how contributions to Roth IRAs can lead to significant tax savings over time, especially for younger investors. The discussion […]
Gifting Strategies to Save on Taxes

Subscribe to Cup of Bull! In this episode of Cup of Bull, Michael Dunham and Patrick Fontana discuss effective strategies for gifting to children, particularly through the lens of business ownership. They explore various methods such as putting kids on payroll, utilizing custodial accounts, and the tax benefits associated with these strategies. The discussion emphasizes […]
Reframing Reality | Lessons on Life and Investing

In this episode of Cup of Bull, Patrick Fontana and Michael Dunham explore the concept of reframing in financial planning and life. They discuss insights from Barry Ritholtz’s book ‘How Not to Invest’, emphasizing the importance of acknowledging uncertainty and valuing time. The discussion transitions into practical financial strategies, including funding Roth IRAs, maximizing HSAs, […]
Navigating Market Downturns

In this episode of Cup of Bull, Patrick Fontana and Michael Dunham discuss the emotional reactions investors face during market downturns and emphasizes the importance of sticking to a well-thought-out investment strategy. They highlights historical market trends, the significance of rebalancing, and smart investment behaviors that can help investors navigate through volatility. Additionally, they provides […]
Financial Planning Considerations when Inheriting Large Sums of Money

In this episode of Cup of Bull, Patrick Fontana and Michael Dunham discuss the complexities of inheriting large sums of money, focusing on the importance of understanding tax implications, strategic financial planning, and the need to approach financial decisions with caution. They emphasize the significance of working with a financial planner to navigate these challenges […]