Category: Business
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)

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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

Resources:

Connect with Josh Leonard: 

Connect with Adam Nash:

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.

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

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

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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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Connect with Pete Belcastro: 

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Juggling Retirement & College Debt with Dan Cieniewicz (Ep. 45)
Juggling Retirement & College Debt with Dan Cieniewicz (Ep. 45)

Juggling Retirement & College Debt with Dan Cieniewicz (Ep. 45)

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Are you nearing retirement but still burdened with your kid’s college debt payments? Discover how you can potentially cut those payments in half with The College Dude.

Today on Relax, It’s Retirement, Josh Leonard and Dan Cieniewicz, CFP®, CCFC, CSLP®, a.k.a. The College Dude, delve into the world of managing Parent PLUS loans to balance funding education and retirement savings effectively. They discuss the nuances of student debt repayment strategies, income-driven repayment plans, the double consolidation loophole, and the impact on retirement planning.

Josh and Dan discuss:

  • Understanding Parent PLUS loans and their underwriting criteria.
  • Exploring income-driven repayment plans for managing student loan debt effectively.
  • Unveiling the double consolidation loophole as a strategy to lower Parent PLUS loan payments.
  • Examining the implications of student loan repayment on retirement income and estate planning.
  • And more

Resources:

Connect with Josh Leonard: 

Connect with Dan Cieniewicz:

About our Guest: 

Dan Cieniewicz works with parents of teenage children as they find themselves in a position to strategize to pay for college while also staying on track for retirement. Dan’s goal when working with clients is to explain the complexities of the financial aid & college application process and to strategize to make sure that both parents and children are set up for long-term success. 

Dan was born & raised in Berks County. He attended Albright College, majoring in Economics & Political Science and played on the football team.  Dan has obtained the CERTIFIED FINANCIAL PLANNER™ designation. 

Dan is the head girls basketball coach at Warwick High School in Lititz, PA and loves working out and playing basketball. He resides in Lititz with his wife, Carly.  He also became a father in March of 2022, to a beautiful daughter, Stella.

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Navigating Financial Storms: Lessons from Market Meltdowns
Navigating Financial Storms: Lessons from Market Meltdowns (Ep. 44)

Navigating Financial Storms: Lessons from Market Meltdowns (Ep. 44)

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Have you ever wondered how quickly the stock market can plunge into a bear market and the impact it has on your investments?

Join Josh Leonard and our Pete Belcastro, as they delve into three significant market crashes in history, including the 1929 stock market crash, Black Monday in 1987, and the recent COVID market meltdown. Discover how fear drives investors, the role of margin accounts, and the importance of long-term investing, even in times of extreme volatility.

Josh and Pete discuss:

  • Historical market crashes: 1929, Black Monday 1987, and the COVID crash in 2020
  • Examining the impact of fear on market behavior and investor decisions
  • Understanding the role of margin accounts and their implications in market downturns
  • Highlighting the importance of staying committed to long-term investing despite market volatility
  • And More!

Resources:

Connect with Josh Leonard: 

Connect with Pete Belcastro: 

 

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Empowering Women in Retirement: The Legacy of Barbara Hillary (Ep. 43)
Empowering Women in Retirement: The Legacy of Barbara Hillary (Ep. 43)

Empowering Women in Retirement: The Legacy of Barbara Hillary (Ep. 43)

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What’s your retirement adventure? Meet Barbara Hillary, the trailblazer who set foot on the North Pole at 76. Let’s explore her remarkable story!

In this special Women’s History Month episode, Josh Leonard and Yana Leonard, CIA, MBA, Director of Finance, share the incredible life story of Barbara Hillary, an inspiring woman who challenged herself to achieve the impossible. From battling cancer to conquering the North Pole at 76, Barbara’s journey is a testament to resilience and determination. Discover how she raised funds, trained rigorously, and embodied the spirit of adventure in retirement, inspiring others along the way. Get ready to be inspired to embrace new horizons and set audacious goals.

Josh and Yana discuss: 

  • How Barbara Hillary conquered the North Pole at 76 and later the South Pole
  • Overcoming health challenges and turning them into inspiration
  • The importance of finding purpose and adventure in retirement
  • Planning for the next chapter in life and empowering women to chase their dreams
  • Embracing new challenges and adventures in retirement
  • And more

Resources:

Connect with Josh Leonard: 

Connect with Yana Leonard:

About our Guest: 

Yana Leonard, CIA, MBA, is the Director of Finance at Leonard Advisory Group. Ms. Leonard has held various finance roles within the manufacturing, pharmaceutical, and food and beverage industries. In her current role, Ms. Leonard delivers strategic recommendations and implements targeted solutions to drive business growth and optimize financial performance. Ms. Leonard earned a bachelor of arts degree in accounting and a minor in economics from Baldwin Wallace University and a masters of business administration (MBA) with a concentration in Accounting. She is a certified internal auditor (CIA). Ms. Leonard grew up in Solon, OH and resides in St. Joseph, MI with her husband Josh, their children, Eli and Isaac, and Layla, a golden retriever. In her spare time, she enjoys attending her kids’ extracurricular activities, traveling, volunteering, reading, and spending time at the lake with friends and family.

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Are Behavioral Biases Affecting Your Retirement Planning & Investment Decisions? (Ep. 42)
Are Behavioral Biases Affecting Your Retirement Planning & Investment Decisions? (Ep. 42)

Are Behavioral Biases Affecting Your Retirement Planning & Investment Decisions? (Ep. 42)

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Have you ever found yourself making financial decisions based on instinct rather than informed choices? 

In this episode, Josh Leonard talks about five common behavioral biases that can influence financial decision-making. He addresses loss aversion, confirmation bias, herd mentality, overconfidence, and anchoring bias, illustrating each with real-world examples. He also discusses the influence of laziness and habit on decision-making and suggests a four-step approach to counteract biases: recognition, education, professional advice, and informed decision-making.

Josh discusses: 

  • Loss aversion and its impact on investment decisions
  • Confirmation bias and its influence on perceptions and decision-making
  • Herd mentality and the potential financial risks associated with following the crowd
  • Overconfidence and its role in guiding risky financial decisions
  • Anchoring bias and its impact on decision-making and perceptions of value
  • Four steps to outsmarting behavioral biases
  • And more

Resources:

Connect with Josh Leonard: 

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Retirement Success Through Discipline and Goal-Setting with Pete Belcastro, CFP® (Ep. 41)
Retirement Success Through Discipline and Goal-Setting with Pete Belcastro, CFP® (Ep. 41)

Retirement Success Through Discipline and Goal-Setting with Pete Belcastro, CFP® (Ep. 41)

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In a world filled with distractions and temptations, discipline stands as a beacon of consistency and success, guiding us toward our goals and aspirations. Whether in financial planning, health routines, or personal growth, discipline forms the foundation for long-term achievement and fulfillment.

Today on Relax, It’s Retirement, Josh and Pete Belcastro, CFP®, talk about discipline in various aspects of life, drawing parallels between maintaining financial discipline and personal habits. Using personal anecdotes, they emphasize the importance of setting realistic goals, committing to long-term strategies, and seeking professional guidance to achieve financial success in retirement. They discuss the three-bucket approach to retirement planning, emphasizing the significance of consistent contributions and staying invested for long-term growth. 

The conversation touches on the value of discipline in navigating market fluctuations and resisting short-term impulses. The episode concludes with insights on the positive impact of discipline in achieving financial goals and the benefit of seeking professional advice for retirement planning.

Key topics include: 

  • The concept of discipline in various aspects of life, including health decisions and financial planning for retirement.
  • Why setting realistic expectations, consistent behavior, and long-term goals to achieve success is important.
  • Discipline’s role in investing, and the need for a disciplined approach to navigate market volatility and achieve financial goals.
  • How discipline can help achieve financial security for retirement.
  • Negative connotations associated with discipline and how it can actually lead to positive outcomes and personal growth.
  • The challenges of maintaining discipline and the benefits of setting disciplined goals
  • And more

Resources:

Connect with Josh Leonard: 

Connect with Pete Belcastro: 

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How to Maximize Your Tax Savings with Pete Belcastro, CFP®
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)

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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:

Connect with Josh Leonard: 

Connect with Pete Belcastro: 

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Navigating Life’s Twists and Turns: A Candid Conversation with Yana Leonard | Family, Finance, and More (Ep. 39)

Navigating Life’s Twists and Turns: A Candid Conversation with Yana Leonard | Family, Finance, and More (Ep. 39)

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Have you ever wondered how successful couples navigate the challenges of marriage, parenthood, and career?

Meet Yana Leonard, CIA, MBA, a key member of the team at Josh Leonard Advisory Group, as she steps into the spotlight in this episode of Relax, It’s Retirement.

Today, Josh introduces his wife, Yana Leonard, CIA, MBA, Director of Finance, to listeners. They dive into the evolution of their relationship from their college days to marriage. Josh and Yana candidly discuss the hurdles they’ve overcome, including the birth of their children and the strain of the COVID-19 pandemic on their family life. 

Knowing the team at Leonard Advisory Group is very important to them. The episode aims to give listeners the opportunity to get to know Yana.

Josh and Yana talk about: 

  • The story of their relationship from college to marriage
  • Challenges faced as a couple, including the birth of their children and the impact of COVID-19
  • Importance of communication, balancing priorities, and finding time for each other
  • Challenges of finding a balance between individual interests, work, and family commitments
  • And more

Resources:

Connect with Josh Leonard: 

Connect with Yana Leonard:

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Navigating Post-Employment 401(k) Options (Ep. 38)

Navigating Post-Employment 401(k) Options (Ep. 38)

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What are the long-term impacts of keeping your 401(k) with a former employer versus rolling it over to an IRA or a new employer’s plan? How can the benefits of IRA rollovers and Roth conversions influence your decision for penalty-free withdrawals?

Josh Leonard explores the advantages and disadvantages of maintaining the 401(k) with a past employer, transitioning it into an IRA, or moving it to the retirement plan of a new employer.  He highlights the importance of comprehending the regulations, costs, and tax consequences associated with each plan. 

Josh discusses: 

  • What are the options for handling a 401(k) with a previous employer
  •  When is it appropriate to roll over a 401(k) to an IRA
  • How do automatic savings and employer matching contributions benefit 401(k) participants
  • What are the potential tax implications and benefits of converting a traditional 401(k) or IRA to a Roth IRA
  • And more

Resources:

Connect with Josh Leonard: 

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