Tax Planning – Wealth on the Move

Custom Indexing for 2025 with Gregory Allison, CFA (Episode 36)

By Wealth on the Move | November 20, 2025

Summary: In this episode of Wealth on the Move, host Will Hoffman and guest Gregory Allison, CFA from Orion Custom Indexing discuss the innovative strategy of custom indexing. They explore how this approach allows investors to manage concentrated stock positions, utilize tax loss harvesting, and enhance after-tax returns. The conversation delves into the technology behind custom indexing, its applications for real estate investors, and the benefits of charitable giving strategies. They also touch on the emergence of custom indexing as a viable option for a broader range of investors, emphasizing the importance of personalized wealth management solutions.

Resources:

Takeaways:

Custom indexing allows for personalized investment strategies.
Tax loss harvesting can enhance after-tax performance.
Utilizing losses can offset future capital gains.
Technology plays a crucial role in executing custom indexing.
Real estate investors can benefit from custom indexing strategies.
Charitable giving can be optimized through custom indexing.
Custom indexing is not suitable for IRA accounts.
The strategy emerged due to advancements in technology.
Concentration risk is a concern for long-term investors.
Longevity impacts investment strategies and tax planning.

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Disclosures:

Gregory Allison Orion Portfolio Solutions are not affiliated with Hoffman Wealth Management and Private Advisor Group.

Wealth management services provided by Orion Portfolio Solutions, LLC (“OPS”), a registered investment advisor. Orion OCIO services provided by TownSquare Capital, LLC (“TSC”), a registered investment advisor. OPS and TSC are affiliates and wholly owned subsidiaries of Orion Advisor Solutions, Inc.

Custom Indexing offered through Orion Portfolio Solutions, LLC a registered investment advisor.

Custom Indexing is an investment strategy wherein a portfolio is managed to mimic an index or other portfolio, while taking into account the tax position, holdings, and individual investing preferences of a client. The performance of a portfolio using custom indexing may vary significantly from the target index (referred to as tracking error or tracking difference), and this variance may increase with greater customization within a portfolio.

Tax-loss Harvesting is a process by which securities trading at unrealized losses are sold to realize a taxable loss. Proceeds from the sales are then used to reinvest in alternate securities to maintain market exposure. Tax-loss Harvesting can be used as a strategy to offset realized gains from other investments and/or carried forward to later calendar years to offset future taxable gains.

This information is general in nature and is not intended as tax advice. You should consult a tax professional as to how this applies to an individual tax situation. Nothing contained herein is intended to constitute accounting, legal, tax, security or investment advice, nor an opinion regarding the appropriateness of any investment, or solicitation of any type.

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Caregiving, Finances, and Family: ‘My Mother’s Money’ and the Hidden Costs of Care w/ Beth Pinsker (Episode 35)

By Wealth on the Move | November 13, 2025

Summary: In this episode of Wealth on the Move, host Will Hoffman speaks with Beth Pinsker, a personal finance columnist and author of ‘My Mother’s Money.’ They discuss the challenges of caregiving, the complexities of financial responsibilities, and the importance of having essential documents in place. Beth shares her personal journey of navigating her mother’s illness and the financial decisions that arose, emphasizing the need for open conversations about money within families. The episode highlights the emotional and practical aspects of caregiving and offers valuable insights for listeners.

Resources:

Takeaways:

Caregiving often intertwines with financial responsibilities.
Bad financial decisions are common in caregiving situations.
Having essential documents like power of attorney is crucial.
Families need to communicate openly about finances.
Financial planning is not just about investments; it’s about life decisions.
The sandwich generation faces unique challenges in caregiving.
Understanding financial structures can prevent future issues.
Storytelling can facilitate important family discussions.
Navigating healthcare and financial systems is complex and often frustrating.
Preparation can alleviate stress during caregiving crises.

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You Can’t Diversify Away Behavior: What Most Investors Get Wrong w/ Felipe Toews (Episode 34)

By Wealth on the Move | November 6, 2025

Summary: In this episode of Wealth on the Move, host Will Hoffman interviews Felipe Toews, CEO of Toews Asset Management and author of ‘The Behavioral Portfolio. They discuss the importance of understanding investor behavior, the impact of market history on investment strategies, and the need for proactive communication in managing portfolios. Toews emphasizes the significance of constructing resilient portfolios that can withstand market chaos and the risks associated with timing the market. The conversation also explores the bucket strategy in portfolio management and the future of behavioral finance.

Resources:

Takeaways:

Investors often rely on outdated portfolio strategies that may not suit their needs.
Understanding investor behavior is crucial for effective portfolio management.
Market history shows that downturns can be more severe than recent experiences suggest.
Constructing portfolios that address both economic realities and investor psychology is essential.
Proactive communication can help investors navigate market volatility.
The bucket strategy can mitigate risks associated with market downturns.
Diversification may not provide the protection investors expect during crises.
Preparing for market chaos involves having a clear plan of action.
Timing the market is a risky strategy that often leads to poor outcomes.
The field of behavioral finance is evolving and offers new insights for investors.

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Phillip Felipe Toews and Toews Asset Management are not affiliated with Hoffman Wealth Management and Private Advisor Group.

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Volatility, Gold, and Staying the Course: Breakdown of Q4 Market w/ Ryan Detrick (Episode 33)

By Wealth on the Move | October 30, 2025

Summary: In this episode of Wealth on the Move, host Will Hoffman and guest Ryan Dietrich discuss the current state of the markets, including insights on volatility, market recovery, and the impact of government shutdowns. They explore the dynamics of the gold market, interest rates, and the Federal Reserve’s outlook, as well as trends in the crypto market. The conversation also delves into behavioral finance and market psychology, emphasizing the importance of having a strategic investment plan. Finally, they provide predictions for future market trends and economic outlooks.

Resources:

Takeaways:

The market has shown resilience despite recent government shutdowns.
Gold is currently overextended, indicating potential for a pullback.
The Federal Reserve is expected to cut interest rates soon.
Historical data suggests that bull markets can last longer than expected.
Behavioral finance plays a significant role in investment decisions.
Investors should be cautious with crypto investments due to volatility.
Market corrections are normal and can present buying opportunities.
The consumer market remains strong despite economic uncertainties.
Global investment opportunities are still available for savvy investors.
Volatility is a necessary aspect of investing that should be embraced.

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Vanguard Proves Why Financial Advisors Matter – And What Most Get Wrong (Episode 31)

By Wealth on the Move | September 26, 2025

Summary: In this episode of Wealth on the Move, host Will Hoffman and director of financial planning Niko Rosso discuss the value that financial advisors bring to their clients, referencing a significant study by Vanguard. They explore various aspects of financial planning, including investment selection, asset location, tax efficiency, and the importance of behavioral coaching. The conversation emphasizes the evolving role of independent financial advisors in a changing financial landscape, highlighting the need for financial literacy and proactive planning.

Resources:

Download the Vanguard Study HERE!

Takeaways:

Vanguard’s study highlights the value of financial advisors.
Investment selection can add significant alpha to portfolios.
Behavioral coaching is crucial for client success.
Understanding asset location can enhance tax efficiency.
Tax loss harvesting can provide financial benefits.
Budgeting is essential for financial discipline.
Independent financial advisors are shaping the future of wealth management.
Financial literacy is vital for effective money management.
Proactive planning can mitigate financial risks.
The evolving landscape of financial advising requires adaptability.

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Connect with Niko Rosso:

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Maximizing Financial Aid: The FAFSA Guide with Tina Steele (Episode 30)

By Wealth on the Move | September 11, 2025

Summary: In this episode of Wealth on the Move, Will Hoffman speaks with Tina Steele, the FAFSA guru, about the intricacies of the FAFSA process and how families can maximize their financial aid opportunities. They discuss the importance of understanding FAFSA, the changes that have occurred recently, and strategies for families to navigate the financial aid landscape effectively. Tina shares insights on common mistakes families make, the significance of documentation, and the future of FAFSA, including new technologies that will aid in the process. This conversation is essential for parents and students preparing for college funding.

Resources:

Takeaways:

FAFSA is crucial for all students attending college.
Filling out FAFSA is necessary every year for financial aid.
Many families mistakenly believe they won’t qualify for aid.
Child support is now treated as an asset in FAFSA calculations.
Families can report special circumstances to financial aid offices.
It’s important to appeal financial aid offers for potential increases.
NIL income can affect financial aid eligibility for student-athletes.
Common mistakes include misreporting assets and missing deadlines.
Documentation is key for the FAFSA process and potential verification.
The FAFSA process is evolving with new technologies for assistance.

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Tina Steele and The FAFSA Guru not affiliated with Hoffman Wealth Management and Private Advisor Group. This presentation is not intended as specific financial advice for any individual.

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The NIL Revolution: Transforming College Sports with Kristi Dosh (Episode 27)

By Wealth on the Move | August 21, 2025

Summary: In this episode of Wealth on the Move, host Will Hoffman and NIL expert Kristi Dosh delve into the transformative landscape of Name, Image, and Likeness (NIL) in college sports. They discuss the evolution of NIL rules, the financial implications for student-athletes, and the importance of building a personal brand through social media. Kristi shares insights on navigating contracts, the role of agents, and the tax responsibilities that come with NIL deals. The conversation also highlights the future of NIL, including market inefficiencies and undervalued opportunities for athletes.

Resources:

Kristi’s Website’s
- Kristidosh.com
- Business of College Sports Website
The Athlete’s NIL Playbook Website
LinkedIn: Sportsbizmiss
Facebook: Kristi Dosh
Instagram: Sportsbizmiss
TikTok: Sportsbizmiss
YouTube: Business of College Sports

Takeaways:

NIL has revolutionized the financial landscape for college athletes.
The rules around NIL have changed significantly since July 2021.
Athletes must navigate a complex and evolving NIL environment.
Written contracts are essential for NIL deals to avoid misunderstandings.
Many athletes may not need agents but should consider hiring attorneys.
Tax implications are a crucial aspect of NIL earnings for athletes.
Social media presence is vital for building a personal brand.
Athletes should diversify their content beyond just their sport.
NIL opportunities can extend into coaching and clinics for athletes.
The future of NIL may see more states allowing high school athletes to participate

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Kristi Dosh and Business of College Sports are not affiliated with Hoffman Wealth Management and Private Advisor Group. Hoffman Wealth Management and Private Advisor Group do not provide tax or legal advice. This presentation is not intended as specific financial, tax or legal advice for any individual. Please consult with qualified professionals for these types of advice.

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All About the One Big Beautiful Bill Act with Tax Wizard Kelly Bender (Episode 26)

By Wealth on the Move | August 14, 2025

Summary: In this episode of Wealth on the Move, host Will Hoffman and tax expert Kelly Bender dive deep into the implications of the new OB3 tax law and what it means for both business owners and individual taxpayers. They explore the importance of understanding business entity structures, the impact of payroll tax updates, and the necessity of long-term tax strategies. Key topics include changes to income tax brackets, retirement account contributions, child tax credits, and state and local tax (SALT) deductions. They discuss the permanence of the Qualified Business Income (QBI) deduction, updates to depreciation rules, and investment incentives such as Qualified Opportunity Zones and qualified small business stock. Kelly shares insights from her upcoming book aimed at helping new entrepreneurs navigate the complexities of starting a business, while also addressing common tax myths and the importance of proactive planning for future generations. Throughout the conversation, they emphasize how OB3’s changes require individuals and businesses to adapt to an evolving tax landscape in order to maximize benefits and maintain compliance.

Resources:

Takeaways:

Many small business owners don’t fully understand their entity structure.
OB3 introduces significant tax code changes impacting individuals and businesses.
QBI deduction is now permanent for small business owners.
Income tax brackets have been adjusted, but many won’t feel the impact.
Retirement contributions are now tied to inflation.
Child tax credit will increase to $2,200 per child by 2025.
New senior deduction of $6,000 for those over 65.
SALT deduction cap increased to $40,000.
Qualified Opportunity Zones can defer or eliminate taxes on gains.
Qualified small business stock offers significant tax benefits.
Payroll tax compliance is essential under new rules.
Depreciation rules now allow faster write-offs for capital investments.
Proactive, long-term tax planning can save money in the long run.
Common tax myths can lead to poor financial decisions.
Asking questions is vital for entrepreneurs starting out.

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Connect with Kelly Bender:

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Navigating Market Volatility | Insights from Q2 with Andrew Opdyke (Episode 25)

By Wealth on the Move | August 7, 2025

Summary: In this episode of Wealth on the Move, host Will Hoffman and Senior Economist Andrew Opdyke discuss the current state of the markets, focusing on the second quarter’s volatility, the Federal Reserve’s stance on interest rates and inflation, the impact of AI on business and investment, and the upcoming midterm elections. They also provide insights into portfolio strategies for the third quarter and reflect on historical lessons that can guide future decisions.

Resources:

Takeaways:

It’s time in the market, not timing the market that matters.
Data-driven insights are crucial for accurate forecasting.
Emotions can lead to irrational market reactions.
The second quarter saw significant market swings due to tariffs.
The Federal Reserve is cautious about cutting rates amid uncertainty.
AI is transforming industries and enhancing productivity.
Historical context is essential for understanding current market dynamics.
Investors should maintain a diversified portfolio.
The U.S. remains a strong place for business growth.
Perspective from history can guide future financial decisions.

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RSAs vs. RSUs: Understanding Your Equity Options (Episode 16)

By Wealth on the Move | March 6, 2025

Summary: In this episode of Wealth on the Move, hosts Will Hoffman and Brynn Tarbuck delve into the complexities of achieving financial independence through equity compensation, specifically focusing on Restricted Stock Awards (RSAs) and Restricted Stock Units (RSUs). They discuss the differences between these two forms of equity compensation, their tax implications, and strategies for maximizing their benefits while avoiding common pitfalls. The conversation emphasizes the importance of planning and understanding the financial landscape to ensure a successful path to early retirement.

Takeaways:

Understanding the FIRE movement is crucial for financial independence.
Equity compensation can be confusing but is essential for early retirement.
RSAs are typically issued by startups, while RSUs are from established companies.
Tax implications differ significantly between RSAs and RSUs.
The 83B election can provide substantial tax savings for RSAs.
Avoid overexposure to company stock to mitigate financial risk.
Missing exercise deadlines can lead to forfeiting valuable stock options.
Lifelong tax planning is vital for managing equity compensation.
Diversifying proceeds from equity compensation is essential for retirement planning.
Planning ahead can prevent unexpected tax bills during retirement.

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