About the Guests:

Alex Caswell is a seasoned wealth planner at RHS Financial with nearly seven years at the firm. He boasts a rich career in finance, having worked previously at Charles Schwab and Fidelity as a trading specialist and advisor. Alex has a personal connection to financial planning, being Latvian-born and having grown up in the U.S., where he developed a passion for helping others with their finances inspired by his mother's experiences. He specializes in comprehensive wealth management services tailored towards high net-worth individuals.

Colby Davis is the portfolio manager at RHS Financial, where he has been working since 2012. With a background in economics and finance, Colby handles day-to-day trading and rebalancing while focusing on maximizing tax efficiency and tax-loss harvesting strategies for clients. Originally from Seattle and now based in San Francisco, Colby negotiated his role at RHS Financial with a memorable elevator pitch and has been instrumental in their strategic financial approaches ever since.

Episode Summary:

In this episode of the Teaching Tax Flow podcast, host Chris Picciurro, alongside guests Alex Caswell and Colby Davis from RHS Financial, delve into advanced capital loss harvesting strategies. Beginning with the importance of tax planning as a year-round activity and transitioning into assessing capital gains and losses, this episode navigates the complexities of maximizing financial outcomes. As segments unfold, listeners gain insights into the intricate workings of these strategies and uncover ways to ethically reduce tax liabilities.

Through the discussion, Alex and Colby share seasoned perspectives on implementing tax-efficient investment tactics, emphasizing retail investors' need to offset capital gains. The conversation enriches understanding of capital loss harvesting—a practice aimed at mitigating tax obligations through strategic asset sales—and explores their proprietary long-short strategy named "Trend," promising increased tax efficiency. The episode weaves both foundational knowledge and innovative approaches, capturing the expertise necessary for effectively responding to high-value capital gain scenarios.

Key Takeaways:

Tax Planning: Recognizing that tax planning is a proactive, year-round activity essential for effective financial management.
Capital Gains and Losses: Understanding that capital gains can be offset by capital losses to reduce tax liabilities, with strategic considerations around realized and unrealized gains.
Trend Strategy: Introducing RHS Financial's advanced Trend strategy, which maximizes tax-loss harvesting through long-short investing without increasing portfolio risk.
Emotional Decision-Making: Highlighting the importance of removing emotion from investing decisions, especially when implementing strategies like capital loss harvesting.
Flexibility in Tax Strategies: Emphasizing the crucial advantage of structuring tax strategies, like the Trend, in anticipation of future capital gains from life events or asset sales.

Notable Quotes:

"Your tax return is a verb, not a noun... the most time compression comes in the fourth quarter."
"We're always looking for different strategies to legally and ethically reduce the tax you pay in your lifetime."
"Without understanding how they can implement that [tax strategy], sometimes to their detriment, they decide to kind of hang out there."
"In a world where there's thousands of stocks and ETFs, it's easy to sell that and buy a new {similar} strategy."
"Real estate, stocks, digital assets...sale of any asset you own could potentially be a capital gain event."

Episode Sponsor:
Sunsets & Dinks
www.teachingtaxflow.com/pickleball
CODE: TTF15

(00:03) - Advanced Strategies for Capital Loss Harvesting and Tax Planning
(03:01) - Exploring Wealth Management and Tax Planning with RHS Financial
(05:35) - Cultural Identity and Sports Allegiances in America
(07:22) - From Elevator Pitch to Portfolio Management at RHS Financial
(10:11) - Strategies for Managing Capital Gains and Losses
(17:04) - Advanced Tax Strategies for Managing Capital Gains and Losses
(24:10) - Leveraging Long-Short Overlays to Manage Portfolio Gains
(25:56) - Proactive Tax Strategies for Managing Capital Gains

Ep. 112 | Capital Loss Harvesting Explained

Teaching Tax Flow: The Podcast