How can you evaluate your advisor’s investment performance? We discuss why it’s an important question to ask, why it’s challenging to answer, and why you should be skeptical if the answer is only about past performance. Investing is different from other disciplines because past performance tends to not persist, even for sophisticated institutional investment managers. We also talk about the ways the industry obfuscates historical benchmark relative performance.

Chapters

00:00 Understanding Performance: The Right Questions to Ask Advisors – why it’s a tough question to answer and why it should be that way

04:30 Asset Allocation and Stock Selection – the two components of a proper performance attribution analysis

08:33 Use Long Run Historical Returns as Expectations1 – to hedge against the emotional power of narratives that surround short-term performance (0-5 years)

11:18 Persistence is the Difference Between Skill and Luck 2, 3 – investing is different than other disciplines because the evidence doesn’t support persistence

21:06 Seeding, Merging and Closing Strategies 4,5 - three ways managers are disguising their true performance

25:17 Taking More Risk Than Benchmark – especially in lower volatility asset classes like bonds, picking a favorable benchmark is a common tactic to be aware of

30:23 Moving the (Benchmark) Goal Posts 6, 7 – underperforming funds change their benchmark to something they historically beat…

33:15 Even Institutions Funds Can’t Find Performance Persistence 1, 8, 9, 10 – they also buy good looking past performance that becomes average performance

40:03 Evaluating Advisors: Did They Do What They Said They Would? – can they explain their process, the decisions behind it, and the resulting performance

48:46-51:44 Pat’s 4 Questions To Ask Advisors – Fees, Diversification, Structure, and Tax-efficiency

Sources

1 What Can We Learn from Elite Endowments? (Greenspring, 2025) - https://youtu.be/2wXKgVGUmyo?si=5hd-pN_GUv_fUtO5

2 SPIVA Persistence Scorecard (2025) - https://www.spglobal.com/spdji/en/spiva/article/us-persistence-scorecard/

3 Fund Landscape (Dimensional 2024)- https://www.dimensional.com/us-en/insights/the-fund-landscape

4 The Arithmetic of Active Management (Sharpe, 1991) - https://web.stanford.edu/~wfsharpe/art/active/active.htm

5 Fund Mergers and Liquidations (Dimensional, 2024) - https://www.dimensional.com/us-en/insights/mergers-and-liquidations

6 How To Beat The Stock Market Without Even Lying (WSJ, 2024) - https://www.wsj.com/finance/investing/stock-market-fund-benchmark-change-11660940613

7 Moving the Goalposts? Mutual Fund Benchmark Changes and Relative Performance Manipulation (Mullally and Rossi, 2024) - https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4145883

8 Performance Persistence in Institutional Investment Management (Busse, Goyal, Wahal, 2006) - https://ssrn.com/abstract=890319

9 Choosing Investment Managers (Goyal, Wahal, Yavuz, 2022) - https://ssrn.com/abstract=3651476

10 Mutual Fund Flows and Performance in Rational Markets (Berk, Green, 2003) - https://papers.ssrn.com/sol3/papers.cfm?abstract_id=383061

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.

In this episode, Marcus Schafer and Patrick Collins discuss the intricacies of generating income in retirement. They explore various strategies for withdrawal rates, the importance of asset allocation, and the role of social security. The conversation emphasizes the need for a comprehensive financial plan that includes tax strategies and the evaluation of income-generating products. The hosts advocate for a diversified portfolio approach to ensure long-term financial stability and flexibility in retirement.

Chapters

00:00 Why 4% Withdrawal Rates Are Optimistic1, 2 – we contrast our findings from episodes on Elite Endowment spending policies (EP #4) and an individual’s safe withdrawal rates (EP #10)

04:37 The Limits of Dividends as Income 3, 4, 5 – the drawbacks of concentrating only on dividends

15:52 Asset Allocation for Retirement – start with how many years of expenses can be covered by your bond allocation

22:13 Incorporating Social Security and Pensions – delaying often means higher withdrawal rates at the beginning but higher probabilities of success in the long run

23:53 Retirement Income Valley Opportunities – maximizing the low tax brackets between retirement and taking social security + required minimum distributions

30:22 Tax Diversification is Key for Retirement Income – unknown future tax rates means a tax optimal decision in the accumulation phase might not be optimal when you reach your withdrawal phase

32:53 Account Withdrawal Order – Taxable first, tax-deferred second, tax-free third?

35:33 Incorporating Social Security – despite future potential changes, delaying often makes the most sense on paper for those in good health with one spouse that earned more

39:20 Evaluating “Boomer Candy” 6, 7, 8, 9, 10, 11, 12 – annuities, high yield, derivative income, buffer strategies and more…

50:20 Summary – we break down the 4 key steps to making a retirement income plan

Sources

1 What Can We Learn From Elite Endowments | Greenstream #4: https://www.youtube.com/watch?v=2wXKgVGUmyo&t=1463s

2 How Much Money Do I Need to Retire | Greenstream #10: https://www.youtube.com/watch?v=PPGYWsn7FFQ&t=1s

3 Global Dividend Paying Stocks: A Recent History (Dimensional 2013): https://my.dimensional.com/asset/35082/global-dividend-paying-stocks-a-recent-history

4 Dividends in the Time of COVID (Dimensional 2020): https://www.dimensional.com/us-en/insights/dividends-in-the-time-of-covid-19

5 A Slice of Dividend Accounting (Dimensional 2024): https://www.dimensional.com/us-en/insights/a-slice-of-dividend-accounting

6 The Truth About Annuities: Why Their Bad Rap is (Mostly) Deserved | Greenstream #7: https://youtu.be/2gGq4lX2yP4?si=fduhVER5a2KoT_AX

7 Why Investors Are Piling Into Funds That Promise Not to Beat the Stock Market (WSJ, 2023): https://www.wsj.com/articles/covered-call-etf-option-income-jpmorgan-global-x-ff5591f7?mod=article_inline

8 These Hot New Funds Are ‘Boomer Candy’ for Retirees (WSJ, 2024): https://www.wsj.com/finance/investing/retirees-boomer-candy-investing-fund-62454210?mod=article_inline

9 These Funds Are Like Candy for Boomers. The Taxes Aren’t (WSJ, 2024): https://www.wsj.com/personal-finance/taxes/boomer-candy-funds-are-hot-the-taxes-are-not-280c41a3

10 ‘Boomer Candy’ Funds: Sweet Treats or Investment Toothache? (Morningstar, 2024): https://www.morningstar.com/columns/rekenthaler-report/boomer-candy-sweet-treats-or-investment-toothache

11 Rebuffed: A Closer Look at Options-Based Strategies (AQR, 2025): https://www.aqr.com/Insights/Perspectives/Rebuffed-A-Closer-Look-at-Options-Based-Strategies

12 Buffer Madness (AQR, 2025): https://www.aqr.com/Insights/Perspectives/Buffer-Madness

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.

Is an 8% withdrawal rate, like Dave Ramsey says, sustainable? Or is it 4%? We unpack one of the top questions retirees have: How Much Money Do I Need to Retire? We reviewed the research on replacement, spending, and withdrawal rates to understand what a sustainable portfolio withdrawal rate is.

Chapters:

00:00 Understanding How Much Money You Need to Retire – finding a better answer than “more”

04:13 Spending vs. Asset Retirement Targets 1,2,3,4 – two sides of the same coin when it comes to calculating how much you need to retire

07:44 How to Calculate Your Retirement Spending 5 – spending decreases but by how much depends on your previous income

14:42 Should the 4% Withdrawal Rule be the 2-3% Range? 6,7,8– we unpack the assumptions and research behind one of the most cited rules of thumbs in personal finance

27:10 Variable Spending Rates 7 – the answer to problems with the 4% Rule and why they are so hard to implement

30:21 The Role of Advisors in Navigating Market Downturns – how a good advisor helps keep investors on track

37:31 Asset Allocation Determines Withdrawal Rate Ability 8 – why taking more equity risk counterintuitively means less risk of running out of money

41:39 Using Withdrawal Rate to Guide Increasing or Decreasing Spending – low withdrawal rates might be a license to spend

Sources:

1 What is a Financial Plan?: https://www.youtube.com/watch?v=y_PX-HyRW-Q&t=267s

2 Retirement Replacement Rates: What and How (Briggs, 2015): https://www.researchgate.net/publication/345818788_Retirement_Replacement_Rates_What_and_How

3 The Retirement Income Equation (Lee, 2013): https://my.dimensional.com/asset/622/the-retirement-income-equation

4 (How Much Should I Save for Retirement (De Santis and Lee, 2013): https://www.dimensional.com/us-en/asset/556/how-much-should-i-save-for-retirement

5 Exploring the Retirement Consumption Puzzle (Blanchett, 2014): https://www.financialplanningassociation.org/article/journal/MAY14-exploring-retirement-consumption-puzzle

6 Determing Withdrawal Rates Using Historical Data (Bengen, 1994): https://www.financialplanningassociation.org/sites/default/files/2021-04/MAR04%20Determining%20Withdrawal%20Rates%20Using%20Historical%20Data.pdf?

7 20 Years of Safe Withdrawal Rate Research—A Literature Review & Practical Applications (Kitces, 2014): https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4445517&utm_source=chatgpt.com

8 The Safe Withdrawal Rate: Evidence from a Broad Sample of Developed Markets (Cederburg, 2023): https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4227132

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.

In this conversation, Marcus Schafer and Patrick Collins explore the complexities of real estate investment, discussing whether a home is an asset or a liability, the expected returns on real estate, the risks involved, and the tax implications of investing in property. They emphasize the importance of understanding market dynamics, leveraging unique skills, and conducting thorough analyses to make informed investment decisions. The discussion also includes a real-life case study to illustrate the practical application of these concepts. 

Chapters

00:00 The Allure of Real Estate as an Investment¹– recapping the highlights from our last episode

02:46 What Returns Should We Expect? – And do we see these expectations realized?

04:34 Advantages of Real Estate Investment – leverage, tax benefits, and tangible investments

10:26 Investment Strategies in Real Estate – the two major strategies we see investors pursue

12:02 The Boom and Bust Cycle of Real Estate – as a result of the combination of illiquid assets, high transaction costs, and leverage

23:09 Opportunity Cost Analysis – how and when to evaluate opportunity costs the right way

26:27 Realistic Inputs Create Realist Outcomes – better to have conservative assumptions with upside than aggressive assumptions with downside

36:33 Profitability Metrics – cap rates and price appreciation as a hope strategy

41:42 Tax Advantages of Real Estate – depreciation, 1031 exchanges, and the important distinction of investors vs dealers

48:02 Applying Theory to Practice: A Real-Life Example – Marcus talks about his recent rent vs sell analysis on his old house

Sources

¹ American Dream: Is Your House Your Greatest Investment? | Greenstream #8 (https://www.youtube.com/watch?v=z-_Eg-hHaPA)

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.

36% of Americans believe owning a house is the greatest investment you can make, but is it? In the 8th episode of Greenstream, we breakdown how many of us overestimate our returns by not factoring in true costs, which can be ~5% per year. After costs, fees, and taxes, real estate returns may be underwhelming but viewing a home as a consumption good also has non-monetary benefits. We evaluate how to make the most of your home as an asset, while avoiding overreaching and concentration risks.

¹ Gallup poll - https://news.gallup.com/poll/645107/stocks-gold-down-americans-best-investment-ratings.aspx

² Shiller real estate data - https://papers.ssrn.com/sol3/papers.cfm?abstract_id=291281

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.

In episode 7 of Greenstream, Marcus Schafer and Pat Collins unpack why annuities, especially those labeled “deferred” or “variable”, often fail investors. Through the lens of the Rosenthal family’s costly mistake, they explore why annuities are so complex, how high fees and opaque terms work against consumers, and when (if ever) annuities make sense. From fear-based sales pitches to hidden tax pitfalls, this episode is a must-listen for anyone considering annuities as part of a retirement plan.

00:00 The Bad Reputation of Annuities¹ – the Rosenthal Family’s foundation lost money, despite stock markets doubling, while the salesperson got rich

04:02 Insurance Isn’t Bought, It’s Sold – how simple sales pitches mask 500+ pages of legalese even Pat struggles to understand

10:04 Annuities’ Intended Purpose² ³ ⁴ ⁵ – longevity insurance has a role and has existed since Ancient Rome

18:46 The Annuity Puzzle³ ⁴ ⁵ – if annuitization solves retirement risks, why don’t more people buy them?

21:09 Deferred Annuities as Accumulation Products – most annuities sold today are hybrids of costly, complex investment/insurance vehicles

28:23 The Hidden Costs of Annuities¹ – how one client underperformed the S&P by 7% per year over 18 years

37:00 Variable Annuities Are the Most Missold – what “guaranteed” riders actually mean when you unpack the contract

42:56 When Annuities Make Sense – only in their purest form (SPIAs), and under guidance of a 100% fee-only, 100% fiduciary advisor

49:25 Tax Implications and Wealth Transfer – ordinary income taxes, no step-up in basis, and painful outcomes for heirs

The Best of What We Researched

¹A Couple Won the Powerball. Investing It Turned Into Tragedy (WSJ, 2024) 

²The History Of Annuities in the United States (Poterba, 1997) 

³2024 Retail Annuity Sales Power to a Record $432.4 Billion (LIMRA, 2025) 

⁴New Evidence on the Money’s Worth of Individual Annuities (Mitchell, 2001) 

⁵The Value of Annuities (Wettstein, 2021)

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.

Is the 2025 stock market downturn driven by economic policies, such as tariffs, different from previous market crashes? We're joined by Justin Brown, Greenspring's Director of Investments, to discuss how this time, like every time, is different, but also how drawdowns and volatility are features, not bugs, of markets that reward long-term investors. We outline how investors should respond depending on the preparedness of their portfolio for an unexpected drawdown at an unknown time. We share how we're responding to find a silver lining that may not last long.

Charts discussed:

Full Webinar on Tariffs' Expected Impact on Prices, Costs, and Expected Returns

Subscribe to Greenspring's Chart of the Week

Chapters

00:00 Tariffs Are Driving Uncertainty1 – tariffs are designed to increase prices and are done for three reasons: revenue, restriction, and reciprocity

04:01 Is This Time Different? 2, 3 – economic policy as a catalyst is unique, but investment markets' forward-looking response based on expected cash flows and risk is consistent

16:00 How Should We Strategically React? 4 – The type of action depends on whether you, your financial plan, and your portfolio were built in anticipation of a market drawdown

27:49 What Tactical Actions Should We Take? – Now is the time to opportunistically implement your plan through dynamic rebalancing, tax loss harvesting, monitoring for refinance opportunities, and evaluating whether to accelerate Roth conversions and gifting strategies

39:19 Markets Reward Long-Term Investors – capital returns to its rightful owners in bear markets

The Best of What We Researched So You Don’t Have To

1 Greenspring’s March 2025 Webinar on Tarrif’s Impact on Prices, Costs, and Expected Returns 

2 Bank Trading Desks Are Minting Money From Trump’s Tariff Chaos (WSJ)

3 Market Returns Through a Century of Recessions (DFA)

4 Lump Sum Investing vs Dollar Cost Averaging (Vanguard)

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.

Are Elite Endowment portfolios and returns replicable for other investors? In this episode we unpack what we can learn from some of the most famous institutional investors: endowments. We discuss how their process is repeatable, but the evidence suggests their performance is not. We discuss the challenges of evaluating performance, the debate between whether they are taking more risk vs different risk to achieve higher absolute performance, how lessons from Moneyball can teach investors to play their own game, and more.

Meet with Greenspring: https://greenspringadvisors.com/contact/

Chapters

00:00 Intro - understanding endowments unique opportunities and constraints

08:04 Performance or Process¹ – process and governance offer more tangible lessons for investors

13:52 Spending Policies¹ – how separation of powers enables sustainable withdrawal rates throughout market cycles

19:53 Asset Allocation Insights², ³, ⁴, ⁵ – the research shows average endowment does not add alpha over simple indexes

27:39 Revisiting the Three Sources of Alpha³, ⁶, ⁷ – the evidence suggests any advantages from endowments do not come from informational alpha, it comes from asset allocation decisions

30:00 What do Elite Institutions Do Differently: Alternatives²,³,⁷ – the real debate is whether they are taking different risk or more risk

36:15 Democratization of Alternative Investments – questions to ask to determine if the alleged benefits of an investment transfer to you as the investor

44:06 Structural Advantages of Endowments – are you the NY Yankees or Oakland A’s? Play your game and you can still be successful

Sources

¹The Interaction of Spending Policies, Asset Allocation Strategies, and Investment Performance at University Endowment Funds (Brown, 2013)

² NACUBO Allocations and Performance (2024)

³ Do (Some) University Endowments Earn Alpha? (Barber, 2013)

⁴ What Does Nevada’s $35 Billion Fund Manager Do All Day? Nothing (WSJ)

⁵ Nevada 2024 Update

⁶ The Three Ways to Beat the Market (And Why Most Investors Don't) | GS #2

⁷ Endowments in the Casino: Even the Whales Lose at the Alts Table (Ennis, 2024)

Greenspring Advisors is a Registered Investment Advisor (RIA) and does not provide tax, legal or accounting advice. This material has been prepared for informational purposes only, and is not intended to provide, and should not be relied on for, tax, legal or accounting advice. You should consult your own tax, legal and accounting advisors before engaging in any transaction. Information contained herein has been obtained from sources considered reliable, but its accuracy and completeness are not guaranteed. 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.

Patrick McQuown joins to discuss exiting your business and innovation in Baltimore. Patrick is a 2x founder and the Executive Director of Entrepreneurship at Towson University, where he leads the StarTUp coworking space, accelerator, and incubator. Pat, Marcus, and Patrick discuss the importance of planning for a transaction in advance, how to execute that plan in a way that fits your goals, and most importantly, what to think about after the sale. They also discuss Patrick’s entrepreneurial journey of operating businesses, advising business owners, and mentoring entrepreneurial ventures. They highlight how the StarTUp is driving innovation in Maryland.

Meet with Greenspring: https://greenspringadvisors.com/contact/

00:00 Intro to Guest Patrick McQuown¹ – 2x founder and now running Towson U’s StarTUp Incubator and Accelerator

02:04 Unlike Any Building in the World² – how the StarTUp is breaking the mold to support innovation in the Maryland way

04:21 Get Your Finances Tight and Right – the importance of getting your house to make sure you don’t end up like FanDuel’s founders who got none of their $450M sale

07:00 Exiting to an Institutional Investor – every word of a 90-page sale document is a right you had and right you lost

08:48 Builder vs. Seller Mentality – don’t take it personally but can this thing print money Now, without You?

11:37 Different Types of Buyers – strategic, private, venture, time wasters, and internal: what do they want?

15:32 Get Your House in Order – look like a dream acquisition, not a fixer upper AND still prepare for buyer shenanigans

19:18 Building a Support Team for Exits – why one of Patrick’s best decisions was to bring an adult into the room who never counted his money, just what’s best for the business

22:24 Understanding Deal Structures – you tell me the price and I’ll tell you the terms

28:07 Telling Your Team – avoid the extremes: you aren’t the town crier, but this isn’t also witness protection

32:11 Managing the Wealth from Your Exit – prepare for the surprise tax bill and Patrick’s wish he 179’d his way to a private jet

36:27 Finding Purpose After an Exit – advice to find a way to stay in the game and Patrick’s evolution to academia to support entrepreneurs at Towson U

40:19 Joint Venture Venture Studio – Towson StarTUps partnership with MedStar to bring Medical Technology inventions to market

42:44 Innovative Ventures Done the Maryland Way – Jbrds children’s shows, Miva bottle + foam roller, Zenjoy relaxation drink, and sleep apnea

45:43 Money is a Bit Like Manure – When you pile it up, it smells, but when you spread it around, it tends to grow things

49:27 Learn more about StarTUp³ – sign up for the newsletter, join events, and use the free space.

Sources

¹ Patrick McQuown’s bio - https://www.towson.edu/campus/partnerships-research/patrick-mcquown.html

² Poets and Quants article on Towson StarTUp - https://poetsandquants.com/2024/10/11/unlike-anything-anywhere-in-the-world-inside-towsons-open-to-all-startup-accelerator/

³ Towson University The StarTUp - https://www.towson.edu/startup/

Greenspring Advisors is a Registered Investment Advisor (RIA) and does not provide tax, legal or accounting advice. This material has been prepared for informational purposes only, and is not intended to provide, and should not be relied on for, tax, legal or accounting advice. You should consult your own tax, legal and accounting advisors before engaging in any transaction.

Meet with Greenspring Advisors: https://greenspringadvisors.com/contact/

What is financial planning? Join us for a conversation on what financial planning done well looks like and how to tell when it’s done for the wrong reasons – typically if the conclusion is to buy a product a salesperson receives a commission on. We discuss the difference between static versus dynamic plans, how your families’ plan is similar and different to a company’s financial plan, and trade-offs in the accumulation and withdrawal phases of life. And more.

Sources

1 Riskiest Day of Your Life – a flashback to Pat’s 2015 article discussing the tradeoffs between short- and long-term risks at retirement. The Riskiest Day Of Your Life

2 Exploring the Retirement Consumption Puzzle – David Blanchett’s (Morningstar) research on declining spending in retirement, despite higher inflation for goods common in retirement https://www.financialplanningassociation.org/article/journal/MAY14-exploring-retirement-consumption-puzzle

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.