Tag: Capital Gains

Direct Indexing and Tax-Loss Harvesting with Angela R. Berkosky (Ep. 209)

Direct Indexing and Tax-Loss Harvesting with Angela R. Berkosky (Ep. 209)

Watching a stock or business grow substantially can feel rewarding, until you start thinking about the tax bill that could come with selling it. For investors with appreciated stock, multiple account types, or proceeds from a major sale, investment decisions and tax decisions can quickly become intertwined.

In this episode, Larry Heller, CFP®, CDFA®, speaks with Angela R. Berkosky, CFA®, MBA, Director of Investment Strategy at Savant Wealth Management, about incorporating taxes into portfolio decisions. They explore how different investments may fit within taxable accounts, traditional IRAs, and Roth IRAs, along with approaches for managing highly appreciated positions. Angela also covers direct indexing, tax-loss harvesting, charitable gifting, exchange funds, and long/short equity strategies that may be considered following a business sale or other significant liquidity event.

Larry and Angela discuss:

  • How taxes can influence investment selection and placement across different account types
  • Ways to address highly appreciated stock while considering diversification and taxable gains
  • How direct indexing may create additional opportunities to capture investment losses
  • Options such as charitable gifting and exchange funds for managing concentrated holdings
  • How long/short equity strategies may help address gains associated with a business sale
  • And more!

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About Our Guest:

Angela Berkosky serves as director of investment strategy, working out of our Lancaster and Wyomissing, Pennsylvania, offices. She has more than 25 years of experience in the financial services industry, with a career rooted in disciplined investment strategy and long-term client outcomes.

Angela began working at Savant in 2023 when Domani Wealth joined the firm. At Domani, she served as partner and chief investment officer beginning in 2010. She led portfolio strategy and investment decision-making across client relationships. Earlier in her career, she worked as an investment officer at a trust company and began her professional path as an associate at a boutique investment bank.

She holds the Chartered Financial Analyst (CFA®) designation and remains actively involved in the profession as a member of both the CFA Institute and the CFA Society of Philadelphia. Her work reflects a commitment to rigorous analysis, thoughtful risk management, and aligning investment strategy with client goals and cash flow needs.

Angela also maintains strong ties to higher education. She serves on the advisory council for the Wood Honors College at Shippensburg University in Pennsylvania, where she mentors honors students and helps guide curriculum and program development. She also serves as secretary of the congregation council at St. John’s Evangelical Lutheran Church in Boyertown, Pennsylvania.

She earned a bachelor’s degree in business administration from Shippensburg University and a Master of Business Administration (MBA) from Lebanon Valley College in Annville, Pennsylvania.

An accomplished pianist, Angela lives in eastern Pennsylvania with her husband, Tom, and their family. They enjoy traveling, attending live concerts, and spending time with their collie, Samson.

Heller Wealth Management is now part of Savant Wealth Management. Savant is a Registered Investment Advisor. This content is provided for informational and educational purposes only and should not be construed as personalized investment advice.

Effective March 31, 2026, Heller Wealth Management joined Savant Wealth Management (“Savant”). A copy of Savant’s current written disclosure Brochure discussing our advisory services and fees is available at www.savantwealth.com/disclosure-brochures/

Unlocking Real Estate Wealth: 1031 Exchanges and DSTs with Stephen Davis [Ep. 157]

Unlocking Real Estate Wealth: 1031 Exchanges and DSTs with Stephen Davis [Ep. 157]

Ready to transform your real estate assets into a tax-efficient retirement plan?

Want to maximize your real estate wealth without the headache of property management?

Join host Larry Heller, CFP®, CDFA®, as he explores the world of 1031 exchanges with Stephen K. Davis, President and CEO of Safe Harbor Asset Management. With over 40 years of experience in financial services, Davis discusses the benefits and intricacies of 1031 exchanges and DSTs, offering valuable insights for property owners and investors.

Key Points Covered:

  • Understanding 1031 exchanges and their role in deferring capital gains taxes
  • Significant tax advantages of 1031 exchanges, including indefinite deferral of taxes
  • How 1031 exchanges reduce property management responsibilities
  • The benefits of Delaware Statutory Trusts (DSTs) for diversifying investments
  • Practical success stories illustrating the benefits of DSTs
  • The importance of tailoring DST investments to meet specific liquidity needs
  • The expected wealth transfer in the real estate market over the next 15 years
  • And much more!

 

Resources:

Connect with Stephen K. Davis:

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About Our Guest:

Stephen Davis, President and CEO of Safe Harbor Asset Management, specializes in tax avoidance strategies, particularly 1031 exchanges. With extensive experience in financial services, Davis provides guidance on transitioning to passive investments and maximizing tax deferral benefits through DSTs. His deep knowledge and practical insights help clients navigate complex real estate transactions and achieve financial security.

HWM Strategies to Save Income Taxes on Your Investments (Ep. 95)

HWM Strategies to Save Income Taxes on Your Investments (Ep. 95)

It’s not what you make but what you keep. Do you know that the taxes you pay on your investments can vary?

Well then, this episode is for you!

In this information-packed episode, Larry Heller discusses diversification, taxes, and different strategies you can use to maximize your return by minimizing your taxes. 

Larry discusses: 

  • What cost basis is and how to lower your capital gains tax
  • How to select the proper method for reducing taxes on your mutual funds
  • Why it’s helpful to know what tax bracket you’re in to save you money
  • Why not knowing about mutual fund distributions and turnover can lead to surprise taxes

Resources: 

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