What do taxes and retirement have in common with your happiest Saturday?
In this episode of Relax, It’s Retirement, Josh Leonard invites you to unravel the often confusing world of taxes as you approach your golden years. He dives into the “tax triangle” strategy, offering a simplified perspective on how to categorize your assets for better tax efficiency.
Josh shares tips on navigating taxed always, taxed later, and the coveted taxed never categories, as well as how these can impact your retirement strategy.
Josh discusses:
The Tax Triangle and how it can guide your financial decisions
The benefits of tax-advantaged accounts like Roth IRAs
Tips for balancing your tax strategy in retirement
Avoiding common tax pitfalls and optimizing for future changes
Goal setting isn’t just for your career—it’s essential for creating an intentional and fulfilling retirement.
What goals will keep you engaged, active, and satisfied as you transition to this next chapter? How do you plan for a successful financial and personal journey during retirement?
In this episode, Josh Leonard recaps his personal and professional goals while emphasizing the importance of intentional goal-setting.
He explores strategies to maintain motivation, improve well-being, and align your finances with your desired lifestyle. By applying the SMART framework, Josh outlines how retirees can structure their aspirations to make retirement a rewarding experience.
Josh discusses:
How achieving his goal of completing the Leadville MTB 100 taught him the value of preparation and persistence
The importance of using the SMART framework (Specific, Measurable, Achievable, Relevant, Time-Bound) when setting personal and financial goals
Examples of how retirees can create income plans, like targeting $6,000 monthly from various sources, to ensure financial stability
Strategies for maintaining healthy habits, such as balancing exercise, diet, and reducing phone time with family
The psychological and emotional benefits of setting goals, including enhanced focus, time management, and overall happiness in retirement
Are you making the most of your year-end tax planning?
In this episode, Josh Leonard dives into effective year-end tax planning strategies to maximize your savings. Prepare for an insightful discussion on Roth conversions, tax loss harvesting, and charitable giving.
Learn how to navigate potential tax pitfalls and make informed financial decisions before the calendar flips to a new year.
Josh covers:
Roth conversions and their tax advantages
Tax loss harvesting to offset gains
Charitable giving strategies, including QCDs and donor-advised funds
Are you maximizing the potential of capital gains and losses in your retirement planning?
This week, Josh Leonard and Pete Belcastro dive into the often-overlooked strategies of capital gain and loss harvesting. You’ll learn the essential differences between capital loss and capital gain harvesting, why timing and tax brackets play a crucial role in your financial planning, and how these strategies can help minimize your tax liability, particularly in retirement.
Join us for an informative discussion that could significantly influence how you manage your investments for a more secure financial future.
Josh and Pete discuss:
Exploring Capital Loss vs. Capital Gain Harvesting: Understanding the fundamental principles and their implications for your tax strategy
Timing is Everything: Why the fourth quarter is critical for reviewing and adjusting your tax planning strategies
Tax Brackets: How these affect your decision-making on selling assets and realizing gains or losses
Retirement Focus: Tailoring these strategies to optimize tax savings and maintain financial health in your golden years
Why does the government force you to take money out of your retirement accounts, even if you don’t need it?
In this episode or Relax, It’s Retirement, Josh Leonard and Pete Belcastro dive into the intricacies of Required Minimum Distributions (RMDs) and explain why they are a crucial aspect of retirement planning. Together, they cover recent changes in RMD rules, including the impact of the Secure Act and the importance of understanding how these changes affect your retirement and tax planning.
You’ll learn about the different types of beneficiaries and the rules surrounding inherited IRAs, making this a must-listen for anyone approaching or navigating retirement.
Josh and Pete discuss:
Understanding Required Minimum Distributions (RMDs) and their recent rule changes
The implications of inheriting an IRA and the different types of beneficiaries
How the Secure Act has changed the way RMDs are calculated and distributed
How to navigate these complex rules and avoid potential penalties
Are you ready to make your retirement last for the long haul?
In this episode of Relax, It’s Retirement, Josh Leonard and Pete Belcastro discuss the importance of longevity in retirement. They cover strategies for structuring your assets to ensure they last, the importance of tax planning, and tips for maintaining an active and fulfilling lifestyle throughout your retirement years. Learn about the three-bucket strategy for managing your funds, the importance of tax-efficient planning, and how staying active and socially engaged can enhance your quality of life.
This episode is packed with valuable tips and real-world examples to help you navigate your golden years with confidence.
Josh and Pete explain:
How to allocate your retirement savings into short-term, income, and growth buckets for long-term stability
Why being tax-efficient now can save you more in the future and ensure your money lasts longer
The importance of staying physically active and socially engaged to improve your quality of life in retirement
How maintaining a routine and engaging in activities can enhance your happiness and longevity
And more
By focusing on longevity, tax efficiency, and staying active in this episode, we want to empower you to make smart decisions for a secure and enjoyable retirement. Listen now and take the first step toward a well-planned future!
Transitioning into retirement could feel just as sunny and relaxed as a perfect summer day, but like spending a day in the sun, you’ve got to plan for all weather factors when it comes to retirement or risk feeling a little burned.
Today on Relax, It’s Retirement, Josh Leonard and Pete Belcastro delve into part two of financial literacy for your golden years with a focus on government benefits and tax planning. In addition to managing required minimum distributions and the timing of Social Security benefits, the conversation also navigates through estate planning and the considerations for relocating or downsizing in retirement. Listen in to empower yourself with the knowledge and strategies needed to embrace retirement with confidence and intention.
Josh and Pete discuss:
Maneuvering the complexities of required minimum distributions (RMDs) and their impact on your taxes
Strategic insights into optimizing Social Security benefits based on individual working and earning scenarios.
The importance of updating beneficiaries and how simple changes can drastically influence estate planning
Navigating the decisions surrounding relocation or downsizing in retirement, including tax implications and quality of life considerations
Are you struggling to navigate the complexities of charitable giving and tax planning for retirement?
Let us introduce you to Daffy!
Josh Leonard and his guest, Adam Nash, co-founder and CEO of Daffy.org dive into the world of donor-advised funds, money decisions, and much more on this engaging episode of Relax It’s Retirement. They address how Daffy can help simplify your giving and give you more control over your charitable donations. Take the stress and guesswork out of charitable giving, allowing you to support causes you care about with ease while maximizing your tax benefits. Find out how Daffy can revolutionize your approach to giving and tax planning.
Josh and Adam discuss:
What donor-advised funds are, and how do they benefit individuals
How Daffy.org is reshaping charitable giving with cutting-edge technology and innovation
The importance of setting financial goals for charitable giving
The impact of automating contributions on financial planning
Benefits of setting giving goals and embracing a donor-advised fund for smarter tax planning and impactful philanthropy
Adam Nash is co-founder and CEO of Daffy.org. Adam is a proven advocate for development of products that go beyond utility to delight customers. At Dropbox, he led the teams responsible for growth, product strategy, product management & product analytics for a platform with over 600 million registered users with responsibility for all of Dropbox self-service revenue (~90% of all company revenue in 2019).
Before Dropbox, Adam served as the President & CEO of Wealthfront, where for four years he championed the creation of a new category of automated investment services. While Adam was at Wealthfront, the company grew its client base by over 60x, and grew assets under management 45x from less than $100m to over $4 billion. During his tenure, Wealthfront delivered industry-leading innovations including Direct Indexing, the Single-Stock Diversification Service, and the first automated 529 College Savings Plan.
Prior to joining Wealthfront, Adam was Vice President of Product Management at LinkedIn. Adam led LinkedIn’s Platform & Mobile products, including the launch of LinkedIn’s open developer platform and their highly successful native applications and mobile web experiences. Adam was the founder and architect of LinkedIn Hackdays, a seminal program for driving the innovation culture at the company. He also was responsible for leading LinkedIn’s search & cloud efforts, as well as forming and leading their user experience & design team.
Prior to joining LinkedIn, Adam held a number of leadership roles at eBay, including Director of eBay Express, an innovative new site focused on new, fixed-price products. Previously, Adam also held strategic and technical roles at Atlas Venture, Preview Systems and Apple.
Adam holds an MBA from Harvard Business School as well as BS and MS degrees in Computer Science with a focus on Human-Computer Interaction from Stanford University.
Adam was born and raised in Silicon Valley where he lives with his wife, four children, and a golden retriever.
Are you looking to maximize your tax bracket and secure a stress-free retirement?
You might want to consider adding Roth conversions to your retirement plan.
Josh Leonard and Pete Belcastro dive into the world of Roth conversions, discussing three key scenarios when converting to a Roth IRA might benefit your retirement plan with a focus on reducing taxes, maximizing income, and securing a tax-efficient legacy for your family.
Josh and Pete discuss:
Maximizing your tax bracket by strategically converting to a Roth IRA to save on taxes in the future
Using Roth funds for emergency or unexpected expenses to avoid high tax implications when tapping into traditional IRAs
Creating a tax-free legacy asset by inheriting a Roth IRA and providing your heirs with a tax-efficient asset
Balancing tax diversification by considering a blend of traditional and Roth IRAs based on your unique financial situation and long-term goals
Tax time is near. Nobody wants to pay taxes, but we have to, so let’s talk about how we can maximize our tax savings.
In this episode, Josh Leonard and Pete Belcastro, Financial Planner at Leonard Advisory Group, talk about tax planning. They share tips for filing taxes this year and some ways to help reduce taxation in the future and be more tax-efficient. Josh and Pete cover the importance of reporting interest from savings accounts, accurately reporting capital gains from stock sales, and the benefits of qualified charitable distributions.
Their conversation also includes strategies for making HSA and IRA contributions to reduce taxable income and the significance of conducting a thorough tax analysis for future savings. Additionally, Josh and Pete explore the pros and cons of traditional versus Roth 401(k)s, tax diversification, Roth conversions, and managing capital gains and charitable giving. They also discuss handling sudden income increases and the use of donor-advised funds for tax-efficient charitable contributions.
Josh and Pete discuss:
Importance of reporting interest earned on savings accounts and capital gains from stock sales for tax purposes
Qualified charitable distributions as a tax-efficient way to donate to charities
Tax implications of qualified accounts and making direct contributions to charities from these accounts
Opportunity to make HSA and IRA contributions before the tax filing deadline to lower taxable income
Benefits of traditional 401(k) versus Roth 401(k) contributions
Strategies for managing capital gains and charitable giving as part of comprehensive tax planning
Importance of proactive tax planning and practical advice for optimizing tax strategies
