Investment returns are expected, not promised. To capture them, investors should both intelligently take risks and stick around for the return. In episode 16 of Greenstream, we break down the psychological and behavioral biases that can hold us back. Investors should view these as penalties or unforced errors that make winning your game harder.

You'll learn:

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

Sources:

1 Are Financial Advisors Worth Their Fee? | Greenstream #13 https://youtu.be/Is7N5M4e4Ck

2 Investment Risk Explained: How Much Diversification Do You Need? | Greenstream #15 https://youtu.be/yEqRrXDAe7A

3 Barberis, Nicholas and Barberis, Nicholas and Thaler, Richard H., A Survey of Behavioral Finance (2002). https://ssrn.com/abstract=327880

4 Barber, Brad M. and Odean, Terrance, Boys Will Be Boys: Gender, Overconfidence, and Common Stock Investment (1998). https://ssrn.com/abstract=139415

5 Barber, Brad M. and Odean, Terrance, Trading is Hazardous to Your Wealth: The Common Stock Investment Performance of Individual Investors. https://ssrn.com/abstract=219228

6 Odean, Terrance, Do Investors Trade Too Much? (1998). https://ssrn.com/abstract=94143

7 Collins, Jim, The Stockdale Paradox. https://www.jimcollins.com/concepts/Stockdale-Concept.html 

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.

Investing isn’t about avoiding risk; it’s about taking the right risks and avoiding the wrong risks. In episode 15 of Greenstream, we break down what risk means, the difference between compensated (right) and uncompensated (wrong) risk, and why most investors underestimate risk.

You’ll learn:

Our next episode will shift from investment to investor risk, where we’ll look at the behavioral challenges of sticking to your investment plan. You can subscribe here.

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 Do Stocks Outperform Treasury Bills? by Hendrik Bessembinder :: SSRN https://papers.ssrn.com/sol3/papers.cfm?abstract_id=2900447

2 JP Morgan’s The Agony and The Ecstasy (2021) https://privatebank.jpmorgan.com/nam/en/insights/latest-and-featured/eotm/the-agony-the-ecstasy

3 JP Morgan’s The Agony and The Ecstasy (2024) https://privatebank.jpmorgan.com/nam/en/insights/markets-and-investing/ideas-and-insights/the-agony-the-ecstasy

4Extreme Stock Market Performers, Part I: Expect Some Drawdowns by Hendrik Bessembinder :: SSRN https://papers.ssrn.com/sol3/papers.cfm?abstract_id=3657604

5 Petajisto, Antti, Underperformance of Concentrated Stock Positions (June 30, 2023): https://ssrn.com/abstract=4541122

6 Fama, Eugene F. and French, Kenneth R., A Five-Factor Asset Pricing Model (September 2014): https://ssrn.com/abstract=2287202

7Harvey, Campbell R. and Liu, Yan and Zhu, Caroline, …and the Cross-Section of Expected Returns (February 3, 2015): https://ssrn.com/abstract=2249314

8 The Three Ways To Beat The Market | Greenstream #2: hhttps://youtu.be/XeGNGWNbF-8

9 Asness, Cliff S. and Frazzini, Andrea and Israel, Ronen and Moskowitz, Tobias J. and Moskowitz, Tobias J. and Pedersen, Lasse Heje, Size Matters, If You Control Your Junk (January 22, 2015): https://ssrn.com/abstract=2553889

10  Rizova, Savina and Saito, Namiko, Investment and Expected Stock Returns (July 8, 2020): https://ssrn.com/abstract=3646575

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.

Is AI overhyped? Or is it the next big leap in productivity and profits? In this episode, we explore real-world examples of how GenAI is transforming small and medium sized businesses. Our guest, Steve Moritz, 2x AI founder and longtime IT consultant, shares how to start using AI in your business, the risks to mitigate, and why leadership buy-in matters. Plus, we discuss what AI’s expected productivity boost means for your investment portfolio.

Steve Moritz: https://www.linkedin.com/in/stephenmoritz/

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

Chapters

00:00 Intro to Steve Moritz - the perfect guest to join as 2x AI Founder and longtime IT implementation consultant

04:10 What is GenAI? - replicative and generative use of data to make decisions

 04:48 Comparing GenAI to Past Tech Shifts - the ability to generate a decision is wholly unique

06:58 Why the Breakthrough Now? - compute capacity has led to an exponential increase in workflow efficiency

11:30 The Biggest Misconceptions of AI - it will not take over the world, but it will reduce clerical jobs

17:35 The 4 Ways Every Small Business Should be Using GenAI Today - to enhance productivity and impact

23:36 Are Employees or Employers Benefiting from Increased Productivity? - this is a key business opportunity

27:09 Prompt Engineering in Hiring- that helps future proof your business

32:08 AI is Like an Employee - humans in the loop processes help plan for, detect, and solve for wrong outputs over time

36:55 Shadow IT - the difference between leveraging off the shelf, internal, and hybrid tools

43:06 AI Privacy, Security, and Transparency - the evolution of the cloud means that it is often safer than employer secured networks

46:59 Data Risk is a Top Concern - garbage in, is garbage out

52:12 Vertical and Horizontal Integration - how AI is changing the job market

59:40 Is AI Overhyped? - it augments your business but doesn’t change it

1:03:14 Small Business Benefits - by leadership endorsing sanctioned uses and finding workflows where data is in motion

1:08:03 How Does AI Affect Investing in the Stock Market? – if the promise is a productivity boost across most industries, AI should be a rising tide that lifts all boats

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

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

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.

Do they add enough value to cover their fee? We dive into to unpacking the qualitative and quantitative components of potential value for investors from fee-only advisors. We also compare fee-only advice with other forms of advice and discuss why investment advice alone isn’t enough to justify 1% per year.

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

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

Chapters:

00:00 Do Advisors Add Value Beyond Their Fee?

03:48 Investor Motivations for Hiring an Advisor1,2 – only 7-12% of investors cite returns as the primary reason they are hiring an advisor

09:41 Quantifying Advisor Value3,4 – the challenges of estimating value that is dependent on actions someone would take otherwise and incorporating nonfinancial factors

12:39 Asset Allocation and Rebalancing5,6,7 – are you taking the right type of risk (diversified) or enough risk?

25:17 Product Selection8,9 – do you know what fees you are paying and if you don’t, it’s probably more than necessary

32:08 Asset Location – matching the tax-efficiency of different investments with the appropriate type of account

40:43 Behavioral Coaching – helping investors understand when they shouldn’t take action and if they should take action, what is it?

50:04 Generating Income in Retirement8 – and avoiding ‘Boomer Candy’ products that prey on the desire for income

53:34 The Importance of Insurance – learning to detect the difference between insurance that protects and insurance that invests, which is typically inefficient

57:11 Tax Planning and Projections – good investment advisors should fill the gap left by tax preparers focused on tax compliance

01:02:16 Commissioned Advice – knowledgeable about the products they sell but incentivized to sell you more than you need

01:07:12 Fee-Only Advice – point in time advice is good but proactive advice unlocks more opportunities to add value

01:13:53 Different People Value Different Things At Different Times – the value of an advisor changes over time

Sources:

1 Why Do Investors Keep Their Advisor Around (Morningstar, 2024): https://www.morningstar.com/financial-advisors/why-do-investors-keep-their-financial-advisors-around

2 Dimensional Investor Study (2021): https://my.dimensional.com/2021-global-investor-study-key-takeaways

3 Vanguard’s Advisor Alpha (2022): https://corporate.vanguard.com/content/dam/corp/articles/pdf/putting_value_on_your_value_quantifying_vanguard_advisors_alpha.pdf

4 Russell’s Value of An Advisor (2025): https://russellinvestments.com/content/dam/ri/files/ca/en/individual-investor/insights/value-of-advisor.pdf

5 Money Doctors (Gennaioli, Shleifer, and Vishny, 2012): https://ssrn.com/abstract=2133429

6 The Three Ways To Beat The Market (Greenspring, 2025): https://youtu.be/XeGNGWNbF-8

7 What Can We Learn From Elite Institutions (Greenspring, 2025): https://youtu.be/2wXKgVGUmyo

8 Generating Retirement Income and the Allure of ‘Boomer Candy’ (Greenspring, 2025): https://youtu.be/Ms8uRmOC6EE 

9 The Truth About Annuities (Greenspring, 2025): https://youtu.be/2gGq4lX2yP4

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

Follow on Spotify: https://open.spotify.com/show/26NYX6WD7godcJAYVE0Yk8

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.

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

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.

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

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.

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

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.

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)

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.

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

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.

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)

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.