Tag: Tax Planning

Capital Loss Harvesting vs. Capital Gain Harvesting: What’s Right for Your Retirement? (Ep. 69)

Capital Loss Harvesting vs. Capital Gain Harvesting: What’s Right for Your Retirement? (Ep. 69)

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
  • And more!

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Navigating RMD Changes for Your Retirement Plan (Ep. 62)

Navigating RMD Changes for Your Retirement Plan (Ep. 62)

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
  • And more

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Longevity in Retirement: Planning for the Long Haul (Ep. 59)

Longevity in Retirement: Planning for the Long Haul (Ep. 59)

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!

 

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Mastering Financial Literacy in Your Golden Years: Part 2 (Ep. 50)

Mastering Financial Literacy in Your Golden Years: Part 2 (Ep. 50)

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
  • And more

Resources:

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Making an Impact with Donor-Advised Funds ft. Daffy.org CEO Adam Nash (Ep. 47)

Making an Impact with Donor-Advised Funds ft. Daffy.org CEO Adam Nash (Ep. 47)

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
  • And more

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About our Guest: 

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.

Maximize Your Retirement: 3 Reasons to Consider Roth Conversions (Ep. 46)

Maximize Your Retirement: 3 Reasons to Consider Roth Conversions (Ep. 46)

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
  • And more

Resources:

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Don’t Let Taxes Crash Your Party – How to Maximize Your Tax Savings with Pete Belcastro, CFP® (Ep. 40)

Don’t Let Taxes Crash Your Party – How to Maximize Your Tax Savings with Pete Belcastro, CFP® (Ep. 40)

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
  • And more

Resources:

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Seven Steps to Successful Retirement (Ep. 36)

Seven Steps to Successful Retirement (Ep. 36)

Is your retirement plan set for a successful future? When was the last time you reviewed your plan and ensured it has been adapted for any life-changing events?

Discover the seven key steps for achieving a fulfilling retirement with Josh Leonard. He touches on everything from crafting a budget and merging accounts to making savvy choices regarding health insurance and maximizing entitlements.

Josh discusses: 

  • What is the first step in building a successful retirement plan
  • When should you start tax planning for retirement
  • Why is understanding Social Security important for retirement
  • How do you approach legacy planning
  • And more

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Is Your End-of-Year Financial Checklist Ready? (Ep. 29)

Is Your End-of-Year Financial Checklist Ready? (Ep. 29)

The end of the year is the perfect time to take stock of your personal finances and make any adjustments that need to be made. 

From catching up on retirement contributions to making charitable donations, you have a bit of time left to get everything in order before 2024. 

In this episode, Josh Leonard explores end-of-year financial planning. He dives into assessing asset and debt issues, understanding tax implications, maximizing contributions to tax-advantaged accounts, and more. Josh also explains the benefits of gifting money to avoid estate taxes and the importance of financial aid planning for children or grandchildren attending college.

Josh discusses: 

  • The need to look at taxable investment accounts and making end-of-year moves
  • The importance of taking required minimum distributions (RMDs) for individuals turning 73 this year
  • Tax planning strategies
  • The importance of maximizing contributions to accounts like HSAs and 401(k)s by the end of the year
  • The need to review insurance plans during open enrollment and update estate documents in light of any family changes or additions
  • The importance of considering financial aid planning strategies for college-bound kids
  • And more!

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Transitioning into Retirement with Jerome Myers (Ep. 17)

Transitioning into Retirement with Jerome Myers (Ep. 17)

Getting stuck doing the things that you’ve always done just because you’ve always done them is one of the biggest atrocities of life. We have an opportunity each day to make something new and you should make the most of it.

In this episode, Josh Leonard brings on Jerome Myers to talk about one of the biggest lifetime transitions, transitioning into retirement. Jerome goes over the key areas of finding your next chapter in life and explains the significance of an “and” instead of an “or” lifestyle, the importance of prioritizing authenticity, how you can find your next mission in life, and how silence can help you find clarity.

Jerome discusses: 

  • Why he started to help people with exit planning and transitioning into retirement
  • The key areas of finding your next chapter 
  • The significance of an “and” lifestyle instead of an “or” lifestyle
  • Why it’s important to prioritize being your true, authentic self in all aspects of your life
  • How he helps people discover their next mission in life
  • How finding silence and peace can help you find clarity
  • And more

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About our Guest: 

Jerome Myers is an award-winning engineer, investor, mentor, and business strategist who helps founders navigate their Exit Paradox through his masterminds and coaching programs.  

Prior to leaving his corporate leadership position, Jerome built a $20 million, 175-person division of a Fortune 550 company from scratch.  He now uses his project management, engineering, and business expertise to advise business leaders on key areas such as leadership strategy, process improvement, sales and data analytics in real estate, financial services, business services, and health care to help his clients double their revenue, time off and charitable giving.

Jerome is also a general partner in a multifamily real estate portfolio and serves on the North Carolina Agricultural and Technical State University Entrepreneurship Advisory Board. 

In 2022, Jerome won the prestigious alumni achievement award for the North Carolina A and T State University College of Engineering where a fully endowed scholarship has been created in his family’s name.  A noted media expert, Jerome has been featured in Business Insider, Black Enterprise, Entrepreneur, Biznow, CBS, ABC, and Fox.

Jerome has interviewed numerous newly exited operators (NEOs) on his top-ranked Dreamcatchers podcast which provides inspiration, education, and direction to his audience of founders who are building companies to sell after they exit the “Matrix”.