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  • Understanding Factor Investing

    Understanding Factor Investing
    Feb 3 2026
    Whether you know it or not, every investor's portfolio takes factor bets. In Episode 26 of Greenstream, we break down what factor investing actually is and how it is used as a framework for understanding risk, diversification, and portfolio construction. You’ll learn: Why factor returns are expected, not guaranteedWhy stocks vs. bonds is the original (and one of the biggest) factors bet investors makeHow factor investing helps distinguish between true manager skill and simply taking more risk to generate performance This episode builds directly on Episode 25, Is Indexing the Best You Can Do?, where we explored why even index investing involves active decisions and why implementation matters. Chapters 00:00 — Understanding Factor Investing(1) Every portfolio reflects factor choices, whether investors realize it or not. 02:17 — What Is Factor Investing and What It Isn’t (1-3) Factor investing means intentionally deviating from market weights to target groups of investments with shared risk and return characteristics, not chasing outperforming stocks. 06:07 — Why Factor Returns Are Expected, Not Promised Factor premiums improve long-term odds, but they are uncertain, volatile, and can underperform the market for long stretches. 12:02 — Why Stocks vs Bonds Is the Original Factor Bet (1) The most widely accepted factor is the market itself: stocks have higher expected returns than bonds, and every investor chooses their exposure. 18:29 — Size and Value: Long-Term Evidence and Tradeoffs (2-3) Smaller and cheaper companies have historically offered higher expected returns, but only for investors willing to tolerate discomfort and tracking error. 30:29 — Momentum: Why Trends Exist (4) Momentum appears consistently in market data, but high turnover, costs, and behavioral challenges make it difficult to capture in practice. 33:44 — Quality: Profitability, Balance Sheets, and Staying Power (5) More profitable companies tend to deliver better outcomes when controlling for size and valuation, helping refine factor exposure. 37:38 — When More Factors Don’t Help Beyond the core factors, many proposed premiums add complexity and cost without meaningfully improving diversification or returns. 40:40 — Common Critiques of Factor Investing (6) Skepticism often stems from recent underperformance, volatility, and the discomfort of looking different from the market. 46:05 — How Investors Actually Implement Factor Tilts Practical implementation starts with understanding current exposures and making thoughtful, diversified adjustments over time. 50:56 — Closing: Better Questions, Not Better Predictions Factor investing isn’t about forecasting winners, it’s about improving decision quality and long-term odds. Follow on Apple Podcasts: https://podcasts.apple.com/us/podcast/greenstream/id1795467982 Follow on Spotify: https://open.spotify.com/show/26NYX6WD7godcJAYVE0Yk8?si=Qxj-H7HiRdGmbNlW8uuV9g Subscribe for Email Updates: https://greenspringadvisors.com/greenstream-podcast Meet with Pat & Marcus: https://outlook.office365.com/book/MarcusCalendaratGreenspringAdvisors@Greenspringos33.onmicrosoft.com Sources Capital Asset Prices: A Theory of Market Equilibrium under Conditions of Risk (Sharpe, 1964)The Cross-Section of Expected Stock Returns (Fama & French, 1992)Common Risk Factors in the Returns on Stocks and Bonds (Fama & French, 1993)Returns to Buying Winners and Selling Losers (Jegadeesh & Titman, 1993)The Other Side of Value: The Gross Profitability Premium (Novy-Marx, 2013)Expected Returns (Ilmanen, 2011) Information contained herein has been obtained from sources considered reliable, but its accuracy and completeness are not guaranteed. It is not intended as the primary basis for financial planning or investment decisions and should not be construed as advice meeting the particular investment needs of any investor. This material has been prepared for information purposes only and is not a solicitation or an offer to buy any security or instrument or to participate in any trading strategy. Past performance is no guarantee of future results.
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    52 Min.
  • Is Indexing the Best You Can Do?

    Is Indexing the Best You Can Do?
    Jan 20 2026
    Index funds have transformed investing. They lowered costs, improved diversification, and helped investors avoid many of the most common mistakes. For most people, indexing has been a clear upgrade over trying to outsmart the market. But even indexing is an active decision. The way an index is built, how it handles income and taxes, and how it’s implemented all influence results in ways that don’t show up in expense ratios. In Episode 25 of Greenstream, we unpack where those decisions live, why they matter, and how investors can keep the intent of indexing while being more thoughtful about execution. You’ll learn about: Why do indices that sound similar have very different expected returnsWhy implementation details can matter as much or more than headline expense ratiosWhen indexing may be appropriate, and how to execute it more thoughtfully 00:00 Is Indexing The Best You Can Do? – why “good enough” investing still deserves scrutiny (1) 01:39 The Evolution of Index Funds – from benchmarking tool to dominant investment strategy (2) 05:46 The Goal of An Index Fund – minimizing tracking error, not beating the market 10:34 Why Indexing Is Still Active – index selection as a subjective decision (3) 13:40 Structural Decisions in Index Construction – S&P 500, QQQ, and what “market” really means (3-6) 16:28 International & Small-Cap Indexes – why similar labels produce very different outcomes (3, 7-8) 21:14 Index Design vs Investor Needs – tax-efficiency and whether an index is built for you (9) 25:50 The Reconstitution Effect – price impact when everyone trades at once (10-12) 34:37 Style Drift Inside Index Funds – how portfolios change between rebalances 37:52 Can Indexing Be Improved? – innovation within rules-based investing 40:02 What Investors Can Do – when indexing is the best option and how to implement it better Follow on Apple Podcasts: https://podcasts.apple.com/us/podcast/greenstream/id1795467982 Follow on Spotify: https://open.spotify.com/show/26NYX6WD7godcJAYVE0Yk8?si=Qxj-H7HiRdGmbNlW8uuV9g Subscribe for Email Updates: https://greenspringadvisors.com/greenstream-podcast Meet with Pat & Marcus: https://outlook.office365.com/book/MarcusCalendaratGreenspringAdvisors@Greenspringos33.onmicrosoft.com Sources 1 – Kissinger: A Biography (Isaacson, 2005) 2 – Trillions: How a Band of Wall Street Renegades Invented the Index Fund and Changed Finance Forever (Wigglesworth, 2021) 3 – Time period: 2021 to 2024. US Index comparisons include average annual returns for CRSP US Total Stock Market Index, S&P Total Market Index, Dow Jones US Broad Stock Market Index, and Russell 3000 Index. Developed ex US index comparisons include average annual returns for FTSE Developed All Cap ex US Index, MSCI EAFE IMI Index (Net), and S&P Developed ex US BMI Index.. Emerging markets index comparisons include average annual returns for S&P Emerging BMI Index (gross div.), MSCI Emerging Markets IMI Index (gross div.), and FTSE Emerging All Cap Total Return Index. 4 – Big Changes For Invesco QQQ: What Investors Should Know (Morningstar, 2025) 5 – NASDAQ-100 Index Methodology 6 – S&P 500 Index Methodology 7 – Opinion: The Hidden Costs of Indexing Are Hurting Institutions’ Returns (Dimensional via Institutional Investor, 2025) 8 – When Tracking Error is a Fix, Not An Error (Dimensional, 2022) 9 - Keeping More of What You Earn: Tax Efficiency of Dimensional Equity Solutions (Dimensional, 2025) 10 - Measuring the Costs of Index Reconstitution: A 10-Year Perspective (Dimensional, 2024) 11 - Tesla’s Charge Reveals Weak Points of Indexing (Dimensional, 2021) 12 - Marlena Lee Discusses Shortcomings of Indexing on “Jill on Money” Podcast (via Dimensional, 2024) Information contained herein has been obtained from sources considered reliable, but its accuracy and completeness are not guaranteed. It is not intended as the primary basis for financial planning or investment decisions and should not be construed as advice meeting the particular investment needs of any investor. This material has been prepared for information purposes only and is not a solicitation or an offer to buy any security or instrument or to participate in any trading strategy. Past performance is no guarantee of future results.
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    49 Min.
  • What 2025 Taught Investors (Even After a Great Year)

    What 2025 Taught Investors (Even After a Great Year)
    Jan 6 2026
    Even after a win, the best coaches go back to the tape. 2025 was a strong year for markets. But like a disciplined coach after a big win, the most valuable work happens in the film review. In Episode 24 of Greenstream, we look back on the year not to celebrate outcomes, but to pressure-test decisions. From tariff-driven volatility to the return of cash as a real option, this episode focuses on the habits that matter when markets don’t cooperate. You’ll learn about: How tariff volatility stress-tested portfolios and what it revealed about discipline, rebalancing, and tax-loss harvestingWhy international stocks outperform in 2025 is a reminder that markets rarely reward forecastsWhat a year of Greenstream conversations revealed, and how that’s shaping where the podcast goes next 00:00 Why Greenstream Exists – better decisions over better predictions 04:36 How We’re Improving the Podcast (1-4) – lessons from past episodes 07:15 Tariffs as a Stress Test (5-7) – what to do during and after volatility 17:07 International Stocks (8-9) – and the limits of forecasting 20:48 Cash is a Decision Again – after yields, taxes, and inflation 28:14 Finding the Middle Ground (10-11) – discipline and diversification 34:31 The New Tax Law (12-13) – more certainty and more complexity 41:02 The Impact of Greenstream (14) – divorcing decisions vs outcomes Follow on Apple Podcasts: https://podcasts.apple.com/us/podcast/greenstream/id1795467982 Follow on Spotify: https://open.spotify.com/show/26NYX6WD7godcJAYVE0Yk8?si=Qxj-H7HiRdGmbNlW8uuV9g Subscribe for Email Updates: https://greenspringadvisors.com/greenstream-podcast Meet with Pat & Marcus: https://outlook.office365.com/book/MarcusCalendaratGreenspringAdvisors@Greenspringos33.onmicrosoft.com Sources 1 Patrick McQuown on Innovation and Exiting Your Business | GS #4 2 GenAI's Impact on Productivity and Profits: With Steve Moritz | GS #14 3 EY’s Lindsay Jordan & Robyn Bew on Why Every Organization Needs a Board (and How to Join One) | GS #18 4 The Business of Baseball with Orioles President Catie Griggs | GS #23 5 Investing through Tariff’s Webinar w/ Economist Apollo Lupescu 6 Is This Time Different – Tariffs | GS #6 7 How Often Should You Rebalance Your Portfolio | GS #22 8 Investment Risk Explained: How Much Diversification Do You Need? | GS #15 9 Is There Still a Case for International Investing? | GS #21 10 Investor Risk: Behavioral Biases That Can Cost Investors Returns | GS #16 11 How To Build The Perfect Portfolio For You | GS #20 12 The Goal of Tax Planning is to Minimize Lifetime Taxes | GS #19 13 Uncovering Opportunities in the New Tax Law "One Big Beautiful Bill Act" Webinar 14 The Truth About Annuities: Why Their Bad Rap Is (Mostly) Deserved | GS #7 Information contained herein has been obtained from sources considered reliable, but its accuracy and completeness are not guaranteed. It is not intended as the primary basis for financial planning or investment decisions and should not be construed as advice meeting the particular investment needs of any investor. This material has been prepared for information purposes only and is not a solicitation or an offer to buy any security or instrument or to participate in any trading strategy. Past performance is no guarantee of future results.
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    52 Min.
  • The Business of Baseball with Orioles President Catie Griggs

    The Business of Baseball with Orioles President Catie Griggs
    Dec 19 2025

    What does it take to run a modern Major League Baseball franchise? In Episode 23 of Greenstream, we talk with Catie Griggs, the Baltimore Orioles’ President of Business Operations, about how the O’s are working to build a championship-caliber fan experience on the field and in the stands. You’ll learn about:

    • Catie’s career path and how 100+ informational interviews helped her break into sports’ apprenticeship-driven industry.
    • The changing economics of professional sports and what it means for team ownership, leadership, and the fan experience.
    • How the Orioles are investing heavily in Camden Yards to modernize the fan experience while preserving what makes it one of baseball’s most iconic ballparks.

    Follow Catie Griggs: https://www.linkedin.com/in/catie-griggs/

    Subscribe for Email Updates: https://greenspringadvisors.com/greenstream-podcast

    Follow on Apple Podcasts: https://podcasts.apple.com/us/podcast/greenstream/id1795467982

    Follow on Spotify: https://open.spotify.com/show/26NYX6WD7godcJAYVE0Yk8?si=Qxj-H7HiRdGmbNlW8uuV9g

    Meet with Pat & Marcus: https://outlook.office365.com/book/MarcusCalendaratGreenspringAdvisors@Greenspringos33.onmicrosoft.com

    Information contained herein has been obtained from sources considered reliable, but its accuracy and completeness are not guaranteed. It is not intended as the primary basis for financial planning or investment decisions and should not be construed as advice meeting the particular investment needs of any investor. This material has been prepared for information purposes only and is not a solicitation or an offer to buy any security or instrument or to participate in any trading strategy. Past performance is no guarantee of future results.
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    41 Min.
  • How Often Should You Rebalance Your Portfolio?

    How Often Should You Rebalance Your Portfolio?
    Dec 4 2025

    Rebalancing may help keep your portfolio aligned with your goals, but how often should you actually do it? In Episode 22 of Greenstream, we break down the research behind rebalancing, why drift matters, and how to use cashflows to rebalance with the least friction and cost. You’ll learn about the:

    • Why rebalancing works and what the evidence shows about managing portfolio drift
    • The tradeoffs between calendar schedules, tolerance-band triggers, and using cashflows to stay aligned with your target mix in an effort to minimize taxes and friction
    • Why a disciplined, rules-based process could help you stay invested during volatile markets

    Subscribe for Email Updates: https://greenspringadvisors.com/greenstream-podcast

    Follow on Apple Podcasts: https://podcasts.apple.com/us/podcast/greenstream/id1795467982

    Follow on Spotify: https://open.spotify.com/show/26NYX6WD7godcJAYVE0Yk8?si=Qxj-H7HiRdGmbNlW8uuV9g

    Meet with Pat & Marcus: https://outlook.office365.com/book/MarcusCalendaratGreenspringAdvisors@Greenspringos33.onmicrosoft.com

    Sources

    1 Opportunistic Rebalancing: A New Paradigm for Wealth Managers (Daryanani, 2008)

    2 Rebalancing and Returns (Dimensional, 2008)

    3 Hong, Xing, Portfolio Rebalancing: Tradeoffs and Decisions (2021): https://ssrn.com/abstract=3858951

    4 Are Advisors Worth Their Fee | Greenstream 13 (2025)

    Information contained herein has been obtained from sources considered reliable, but its accuracy and completeness are not guaranteed. It is not intended as the primary basis for financial planning or investment decisions and should not be construed as advice meeting the particular investment needs of any investor. This material has been prepared for information purposes only and is not a solicitation or an offer to buy any security or instrument or to participate in any trading strategy. Past performance is no guarantee of future results.
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    51 Min.
  • Is There Still a Case for International Investing?

    Is There Still a Case for International Investing?
    Nov 20 2025

    After 15 years of U.S. outperformance, many investors are wondering whether global diversification is still worth it. In Episode 21 of Greenstream, we look past recent returns and dig into the long-run evidence of global stock market returns. You’ll learn about:

    • The academic, risk-adjusted case for international diversification
    • How global diversification helps protect against a ‘lost decade’ or more in your home country
    • The case for home bias and how to build a portfolio you can stick with

    Subscribe for Email Updates: https://greenspringadvisors.com/greenstream-podcast

    Follow on Apple Podcasts: https://podcasts.apple.com/us/podcast/greenstream/id1795467982

    Follow on Spotify: https://open.spotify.com/show/26NYX6WD7godcJAYVE0Yk8?si=Qxj-H7HiRdGmbNlW8uuV9g

    Meet with Pat & Marcus: https://outlook.office365.com/book/MarcusCalendaratGreenspringAdvisors@Greenspringos33.onmicrosoft.com

    Sources

    1Chambers, David and Dimson, Elroy and Ilmanen, Antti S. and Rintamäki, Paul, Long-Run Asset Returns. Available at SSRN: https://ssrn.com/abstract=5022480

    2UBS Investment Returns Yearbook 2025: https://www.ubs.com/global/en/investment-bank/insights-and-data/2025/global-investment-returns-yearbook-2025.html

    3International Diversification—Still Not Crazy after All These Years. AQR, 2023: https://www.aqr.com/Insights/Research/Journal-Article/International-Diversification-Still-Not-Crazy-after-All-These-Years

    4Japan in the News, But It’s Nothing New. Dimensional, 2024: https://www.dimensional.com/us-en/insights/japan-in-the-news-but-its-nothing-new

    5A Tale of Two Decades: Lessons for Long-Term Investors. Dimensional, 2020: https://www.dimensional.com/us-en/insights/a-tale-of-two-decades

    6Has Australia Really Had a 28-Year Expansion? Federal Reserve Bank of St. Louis, 2019: https://www.stlouisfed.org/on-the-economy/2019/september/australia-28-year-expansion

    7Investor Risk: Behavioral Biases That Cost Investors Returns. Greenspring Advisors, 2025: https://youtu.be/jMxlCOdjkqg?si=CzWk2vQ6QEJUyW3P

    8Global Diversification Still Requires International Securities. Dimensional, 2024: https://www.dimensional.com/us-en/insights/global-diversification-still-requires-international-securities

    Greenspring Advisors is a registered investment adviser with the SEC and does not provide tax, legal or accounting advice. Information contained herein has been obtained from sources considered reliable, but its accuracy and completeness are not guaranteed. It is not intended as the primary basis for financial planning or investment decisions and should not be construed as advice meeting the particular investment needs of any investor. This material has been prepared for information purposes only and is not a solicitation or an offer to buy any security or instrument or to participate in any trading strategy. Past performance is no guarantee of future results.
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    44 Min.
  • How To Build The Perfect Portfolio For You

    How To Build The Perfect Portfolio For You
    Nov 6 2025

    It’s one of the most important decisions in personal finance. Research has shown that asset allocation, not the stocks you pick, explains 90% of returns (see sources below). That’s why getting your mix of stocks to bonds right matters most. In Episode 20 of Greenstream, we explain why there is no agreement on the single, optimal portfolio, but how we can find the best portfolio for you.

    You’ll learn about:

    • How to align your portfolio with your risk tolerance, capacity, and need
    • Why your asset allocation should evolve as you approach, are in, and continue through retirement
    • The role ample liquidity plays in building the perfect portfolio for you – one you can stick with

    Subscribe for Email Updates: https://greenspringadvisors.com/greenstream-podcast

    Follow on Apple Podcasts: https://podcasts.apple.com/us/podcast/greenstream/id1795467982

    Follow on Spotify: https://open.spotify.com/show/26NYX6WD7godcJAYVE0Yk8?si=Qxj-H7HiRdGmbNlW8uuV9g

    Meet with Pat & Marcus: https://outlook.office365.com/book/MarcusCalendaratGreenspringAdvisors@Greenspringos33.onmicrosoft.com

    Sources

    1 Brinson, G. P., Hood, L. R., & Beebower, G. L. (1986). Determinants of Portfolio Performance. Financial Analysts Journal, 42(4), 39–44. https://doi.org/10.2469/faj.v42.n4.39

    2 Ibbotson, Roger G. and Kaplan, Paul D., Does Asset Allocation Policy Explain 40, 90, 100 Percent Of Performance?. Available at SSRN: https://ssrn.com/abstract=279096

    3 https://youtu.be/CFbvuB4o1bk?si=HjtiukEtteLJuNAQ

    4 Gennaioli, Nicola and Shleifer, Andrei and Vishny, Robert W., Money Doctors (June 11, 2012). Chicago Booth Research Paper No. 12-39, Fama-Miller Working Paper, Available at SSRN: https://ssrn.com/abstract=2133429 or http://dx.doi.org/10.2139/ssrn.2133429

    5 https://youtu.be/y_PX-HyRW-Q?si=ISVpYmGFudUcYr9O
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    49 Min.
  • The Goal of Tax Planning is to Minimize Lifetime Taxes

    The Goal of Tax Planning is to Minimize Lifetime Taxes
    Oct 23 2025

    Taxes are one of your largest lifetime expenses, but most people think about them after it’s too late to make a difference. In Episode 19 of Greenstream, we break down the difference between tax preparation (filling out your tax return) and tax planning (proactively shaping your outcomes). You’ll learn about:

    • How to identify opportunities before year-end that may disappear in January
    • Why financial advisors and CPAs play complimentary roles in tax strategy
    • Why reducing the tax drag of your investment portfolio is an integral part of tax planning

    Uncovering Opportunities in the New Tax Law "One Big Beautiful Bill Act" Webinar

    Greenspring Advisors is a registered investment adviser with the SEC and only transacts business in states where it is properly registered, or is excluded or exempted from registration requirements. The social media platforms associated with this name are solely for informational purposes and do not offer advisory services or sales of securities. Investing involves risk and possible loss of principal capital. Comments by viewers and/or recognitions are no guarantee of future investment outcomes and do not ensure that a viewer will experience a higher level of performance or results. Public comments posted on this site are not selected, amended, deleted, or sorted in any way. If applicable, certain editing of personal identifiable information and misinformation may be deleted. Content may be dated. Links to third-party sites, or information is from a reasonably reliable source. Information presented on this program is believed to be factual and up-to-date, but we do not guarantee its accuracy, and it should not be regarded as a complete analysis of the subjects discussed. Discussions and answers to questions do not involve the rendering of personalized investment advice, but are limited to the dissemination of general information. A professional advisor should be consulted before implementing any of the options presented. Guests and firms mentioned are not affiliated with Greenspring Advisors. No compensation was provided or received for appearance. Views are those of the speakers as of the recording date.
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    56 Min.