Gen X – 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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How Should I Be Invested When Retired? (Episode 32)

By Wealth on the Move | October 16, 2025

Summary: In this episode of Wealth on the Move, host Will Hoffman discusses the critical aspects of wealth management, particularly for retirees. He emphasizes that the question of how to invest should not be the primary concern; instead, understanding the need for liquidity and planning for both short-term and long-term financial goals is essential. Hoffman outlines strategies for securing income during retirement, the importance of maintaining a disciplined investment approach, and the need to navigate the distribution phase effectively. He encourages listeners to focus on long-term strategies rather than seeking quick stock tips, highlighting the importance of planning for future expenses and potential market fluctuations.

Takeaways:

The question of how to invest is often misguided.
Liquidity is crucial for retirees to enjoy their time.
Market timing is not a reliable strategy.
Investing should be based on long-term goals.
Retirement income should be secured for the short term.
The distribution phase of retirement is critical and challenging.
Good investment ideas take time to develop.
Discipline in investment strategy is essential for peace of mind.
Planning for inflation is necessary for long-term success.
Avoid the temptation of chasing hot stock tips.

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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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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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Fitness & Finance: How Discipline Builds Wealth and Wellness with Stan Vaccari (Episode 24)

By Wealth on the Move | July 24, 2025

Summary: In this episode of Wealth on the Move, host Will Hoffman sits down with fitness expert Stan Vaccari to explore the deep parallels between physical fitness and financial wellness. Together, they discuss how both pursuits demand discipline, accountability, and a long-term strategic mindset. Vaccari draws from his experience in health coaching to emphasize the value of online coaching, the importance of tracking progress, and the common hurdles faced when starting new fitness or financial goals. The conversation touches on the underrated power of walking, post-workout nutrition strategies, and the lifelong benefits of investing in oneself. Reflecting on personal choices and growth, Will and Stan also delve into how historical perspectives shape current trends — including the evolving role of AI in our lives. Like training for a marathon or building wealth, success is best achieved with patience, consistency, and purpose.

Resources:

SV Coaching Website

Takeaways:

Fitness and finance are interconnected and influence each other.
Online coaching can provide better accountability and results than in-person training.
Discipline in training leads to improvements in other areas of life.
Starting points in fitness and finance are often the most challenging.
Setting clear goals and engineering a plan is crucial for success.
Slow and steady progress is more sustainable than quick fixes.
Accountability is key to maintaining fitness and financial goals.
Boring routines can lead to significant results over time.
Measuring progress is essential in both fitness and finance.
You don’t need expensive gadgets to track your fitness effectively.
Walking is a powerful fitness habit that can significantly reduce health risks.
Post-workout nutrition can be unconventional yet effective.
Investing in personal development is crucial for long-term success.
Life choices, such as education paths, can shape future opportunities.
Understanding and utilizing AI is essential for future success.

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Connect with Stan Vaccari:

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Travel Free, Live Rich: Unlocking the Freedom Lifestyle with the Lockwoods (Episode 23 / Part 2)

By Wealth on the Move | July 17, 2025

Summary: In Part 2 of this inspiring conversation, host Will Hoffman dives deeper with Phil and Erin Lockwood, the power couple behind Always Be Changing. This episode explores how they turned their adventurous lifestyle into a sustainable business model. They share how they monetized their YouTube channel, built income streams through brand partnerships, and revived the travel agency model with ABC Trips. Phil and Erin also unveil their online course, ‘Travel Free, Live Rich,’ aimed at helping families learn how to design, fund, and fully embrace a semi-nomadic life. From emotional parenting insights to tactical monetization advice, this episode is packed with practical wisdom for anyone dreaming of breaking the mold and living more freely.

Resources:

Takeaways:

Monetizing content goes beyond YouTube ads—brand deals and direct services are more lucrative.
ABC Trips offers personalized, relationship-driven travel planning with hands-on support.
Travel agents are resurging in popularity due to value-added experiences and human-level service.
Their online course ‘Travel Free, Live Rich’ teaches practical steps to fund and sustain global travel.
Content creation began casually but evolved into a key income stream through consistency and authenticity.
Most brand opportunities come inbound through email after building credibility and audience.
Loyalty programs and travel hacking make luxury experiences accessible with planning.
They emphasize doing it now—before kids are grown, not waiting until retirement.
Immersive travel (e.g. rice harvesting in the Philippines) creates lifelong family memories.
The biggest fear? Not money—but whether their parenting choices truly served their kids long-term.

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Connect with The Lockwoods:

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Nomadic Living with Kids | The Lockwoods’ Journey to Intentional Wealth & Freedom (Episode 22/ Part 1)

By Wealth on the Move | July 10, 2025

Summary: In this episode of Wealth on the Move, host Will Hoffman sits down with Phil and Erin Lockwood—founders of the ‘Always Be Changing’ brand. What began as a shift in educational choices for their children quickly blossomed into a transformational lifestyle change that saw their family exploring all seven continents. The Lockwoods share how they built a life that defies traditional templates—embracing asynchronous cyber schooling, running a remote business, and choosing meaning over money. They explain the philosophy behind their brand, how the pandemic shifted their priorities, and why their adventures are rooted in personal freedom and creative fulfillment. This episode offers a bold take on redefining wealth, education, and how we spend our most valuable resource—time.

Resources:

Takeaways:

The Lockwoods intentionally rejected the traditional 9-to-5 lifestyle to design a life rooted in experience.
They homeschool their children via Ignite Learning Academy, prioritizing flexibility and self-paced learning.
COVID-19 was a key catalyst in realizing that traditional systems (work, school) no longer served their goals.
They maintain a home base in Denver while traveling extensively—a semi-nomadic lifestyle.
Phil continues to run his marketing agency remotely while Erin contributes through content and education.
‘Always Be Changing’ originated from Phil’s company culture but evolved into a lifestyle brand and philosophy.
Off-season travel helped make their global journey surprisingly affordable.
They consciously chose experience and presence with their children over financial maximization.
Erin finds joy and purpose in public storytelling, both as a novelist and vlogger.
Monetization was never the initial goal—but has become a fruitful part of their global journey.

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Connect with The Lockwoods:

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