In this episode of The Engineer Investor Podcast, we delve into William J. Bernstein's classic investing guide, The Four Pillars of Investing: Lessons for Building a Winning Portfolio. Join Engineer Investor as we break down Bernstein’s four pillars—Theory, History, Psychology, and the Business of Investing—and explore how each applies to modern systematic and quantitative investing. We discuss foundational concepts like diversification and asset allocation, examine market history, and address how behavioral biases impact investor decisions. For anyone interested in bridging traditional finance wisdom with a data-driven approach, this episode is a must-listen.

Listener Note: This episode has been updated since its original release.

My Free Personal Finance Guide: ⁠⁠⁠⁠⁠⁠https://github.com/engineerinvestor/personal-finance-guide/blob/main/A_Friendly_Guide_to_Personal_Finance_and_Investing_for_Everyone.ipynb ⁠⁠⁠⁠⁠⁠

Twitter: ⁠⁠⁠⁠⁠⁠https://twitter.com/egr_investor⁠⁠⁠⁠⁠⁠

GitHub: ⁠⁠⁠⁠⁠⁠https://github.com/engineerinvestor⁠⁠⁠⁠⁠⁠

Instagram: ⁠⁠⁠⁠⁠⁠https://www.instagram.com/engineerinvestor/⁠⁠⁠⁠⁠⁠

LinkTree: ⁠⁠⁠⁠⁠⁠https://linktr.ee/engineerInvestor⁠⁠⁠⁠⁠

Disclaimer: As always, these opinions are for educational purposes only and do not constitute investing, legal, or tax advice. Implementation of these strategies requires extensive professional guidance. The tax code's complexity and lack of explicit guidance in many areas creates significant compliance risk. Investors must conduct thorough due diligence and obtain professional advice before attempting any tax-focused trading strategy.

In this episode, we dive into tax-aware long-short factor strategies, a powerful tool for investors seeking substantial net capital losses alongside attractive pre-tax returns. We explore how these strategies differ from traditional loss-harvesting approaches by focusing on deferring short-term capital gains and leveraging the high turnover of factor-based models to realize losses naturally. Through insights on managing short positions, balancing alpha with tax efficiency, and eventually transitioning to a long-only portfolio, we examine the mechanics that drive these strategies’ unique tax advantages. Drawing on AQR Capital Management's research, we uncover simulation results showing how tax-aware strategies can achieve cumulative net capital losses exceeding the initial investment, setting them apart from tax-agnostic approaches. This episode is ideal for financial advisors, tax-savvy investors, and anyone intrigued by sophisticated tax-efficient strategies that can boost after-tax returns.

My Free Personal Finance Guide: ⁠⁠⁠⁠⁠https://github.com/engineerinvestor/personal-finance-guide/blob/main/A_Friendly_Guide_to_Personal_Finance_and_Investing_for_Everyone.ipynb ⁠⁠⁠⁠⁠

Twitter: ⁠⁠⁠⁠⁠https://twitter.com/egr_investor⁠⁠⁠⁠⁠

GitHub: ⁠⁠⁠⁠⁠https://github.com/engineerinvestor⁠⁠⁠⁠⁠

Instagram: ⁠⁠⁠⁠⁠https://www.instagram.com/engineerinvestor/⁠⁠⁠⁠⁠

LinkTree: ⁠⁠⁠⁠⁠https://linktr.ee/engineerInvestor⁠⁠⁠⁠

Disclaimer: As always, these opinions are for educational purposes only and do not constitute investing, legal, or tax advice. Implementation of these strategies requires extensive professional guidance. The tax code's complexity and lack of explicit guidance in many areas creates significant compliance risk. Investors must conduct thorough due diligence and obtain professional advice before attempting any tax-focused trading strategy.

In this episode of The Engineer Investor Podcast, we dive deep into one of the most powerful retirement savings strategies available to high-income earners: the Mega Backdoor Roth 401(k). If you're looking to maximize your retirement contributions and unlock the potential for tax-free growth on a much larger scale, this episode is for you.

We'll answer the most pressing questions about the Mega Backdoor Roth:

1. What exactly is a Mega Backdoor Roth? Discover how this strategy leverages after-tax contributions to let you contribute beyond traditional limits, bypassing Roth IRA income restrictions.

2. How does it work step-by-step? We break down the process, from maximizing your standard 401(k) contributions to converting after-tax dollars to a Roth 401(k) or Roth IRA for long-term, tax-free growth.

3. Why should high earners consider it? Learn why this strategy can be a game-changer for those who want to grow retirement assets tax-free, especially if they’re above the income limits for Roth IRAs.

4. What are the tax implications? From understanding the tax treatment of after-tax contributions to the importance of timely conversions, we’ll discuss what you need to know to avoid unexpected liabilities.

5. Who is eligible, and is this strategy at risk? Not all 401(k) plans support Mega Backdoor Roths. We’ll walk through the requirements and discuss the possibility of future legislative changes.

6. The downsides and criticisms: We cover the complexity, potential costs, and some of the criticisms aimed at this strategy and why consulting a tax professional is highly recommended.

Whether you’re an experienced investor or just getting started, this episode provides valuable insights into an advanced strategy for maximizing tax-free retirement savings.

Tune in to see if a Mega Backdoor Roth could be a fit for your retirement goals!

My Free Personal Finance Guide: ⁠⁠⁠⁠https://github.com/engineerinvestor/personal-finance-guide/blob/main/A_Friendly_Guide_to_Personal_Finance_and_Investing_for_Everyone.ipynb ⁠⁠⁠⁠

Twitter: ⁠⁠⁠⁠https://twitter.com/egr_investor⁠⁠⁠⁠

GitHub: ⁠⁠⁠⁠https://github.com/engineerinvestor⁠⁠⁠⁠

Instagram: ⁠⁠⁠⁠https://www.instagram.com/engineerinvestor/⁠⁠⁠⁠

LinkTree: ⁠⁠⁠⁠https://linktr.ee/engineerInvestor⁠⁠⁠⁠

As always, these insights are for informational purposes only and do not constitute investing, legal, or tax advice—please consult a financial professional to determine what’s best for you.