The Decision Dividend

The headline was simple: happiness reaches a point of diminishing returns around $75,000 of income. The research that followed revealed a more complicated reality in which additional income can still improve well-being, but not equally for everyone or in every circumstance.
In Episode 40 of The Decision Dividend, Pat Collins and Marcus Schafer explore what the evolving evidence can teach us about money, happiness, and the meaning of “enough.”
You’ll learn:
What the original $75,000 happiness study actually found and how newer research changed its interpretation
The one question Pat asked to get his family talking about money and why the same dollar can represent security, freedom, or generosity to different people
How high earners and millionaires can make more intentional financial decisions, including whether to work longer, spend more, or use their wealth to create greater belonging and purpose
For a deeper look at the financial side of defining enough, revisit Episode 10, How Much Money Do I Need to Retire?
 
Chapters
00:00 Can Money Buy Happiness? (1, 2, 3)
03:37 Measuring Happiness and the Famous $75,000 Finding (1)
10:44 What Does “Enough” Really Mean?
15:50 How Income Affects Happy and Unhappy People Differently (2, 3)
18:29 Wealth, Luck, and Gratitude
22:31 Security, Belonging, and Purpose
27:25 What Does Money Mean to You?
31:12 How High Earners and Millionaires Can Think About Spending
35:41 Buying Back Time and Strengthening Relationships
40:17 Should You Work One More Year?
 
Sources
Daniel Kahneman and Angus Deaton, “High Income Improves Evaluation of Life but Not Emotional Well-Being,” Proceedings of the National Academy of Sciences, 2010https://www.pnas.org/doi/full/10.1073/pnas.1011492107
Matthew A. Killingsworth, “Experienced Well-Being Rises with Income, Even Above $75,000 per Year,” Proceedings of the National Academy of Sciences, 2021https://www.pnas.org/doi/full/10.1073/pnas.2016976118
Matthew A. Killingsworth, Daniel Kahneman, and Barbara Mellers, “Income and Emotional Well-Being: A Conflict Resolved,” Proceedings of the National Academy of Sciences, 2023https://www.pnas.org/doi/10.1073/pnas.2208661120
 
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Sources include Kahneman and Deaton (2010), Killingsworth (2021), and Killingsworth, Kahneman, and Mellers (2023). These studies report population-level associations between income and self-reported well-being; they do not establish causation or predict results for any individual. Study measures, samples, and income levels differ.
This discussion is for educational purposes and is not individualized investment, tax, or legal advice. Financial planning involves assumptions and cannot assure that goals will be achieved. Individual circumstances and outcomes vary. The examples and heuristics referenced are illustrative rules of thumb, not planning 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. This discussion is for educational purposes and is not individualized investment, tax, or legal advice. Financial planning involves assumptions and cannot assure that goals will be achieved. Individual circumstances and outcomes vary.

Have markets and technology advanced enough that investors should consider owning the individual stocks in an index rather than investing through a pooled vehicle such as an ETF or mutual fund?
In Episode 39 of The Decision Dividend, we’re joined by Brant Cavagnaro to explore how direct indexing works, who may benefit most, and when a low-cost commingled fund may still be the better choice.
You’ll learn:
What distinguishes direct indexing from an ETF, mutual fund, or traditional separately managed account
How direct indexing may turn tax drag into potential tax alpha, even in rising markets
Which investors may benefit most from personalizing portfolios, harvesting losses, offsetting large gains, and donating appreciated securities
The limits of direct indexing, from the downsides of personalization to tax benefits that may fade over time
Sources
Shomesh E. Chaudhuri, Terence C. Burnham, and Andrew W. Lo, “An Empirical Evaluation of Tax-Loss-Harvesting Alpha,” Financial Analysts Journal, 2020https://rpc.cfainstitute.org/research/financial-analysts-journal/2020/0015198x-2020-1760064
Vanguard, “Tax-Loss Harvesting: Why a Personalized Approach Is Important”https://corporate.vanguard.com/content/dam/corp/research/pdf/tax_loss_harvesting_why_a_personalized_approach_is_important.pdf
Libor Gromis, Nathan Sosner, and Steven Krasner, “The Tax Benefits of Direct Indexing: Not a One-Size-Fits-All Strategy,” AQRhttps://www.aqr.com/Insights/Research/Journal-Article/The-Tax-Benefits-of-Direct-Indexing
Savina Rizova and Mark Krasniewski, “A Historical Perspective on Multifaceted Tax Management,” Dimensional Fund Advisors, 2025https://www.dimensional.com/us-en/insights/a-historical-perspective-on-multifaceted-tax-management
For a broader look at how direct indexing fits alongside other investment innovations, revisit Episode 27, The Future of Investment Management:https://www.youtube.com/watch?v=NktNNSc44NM&t=492s
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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.
 

Retirement is a natural time to rethink where you live. But moving states is not just a tax decision.
In Episode 38 of The Decision Dividend, Pat and Marcus discuss how to evaluate a retirement move by starting with quality of life, then running the numbers. The goal is not to ignore taxes, but to understand them in the context of your actual retirement income, residency, housing, insurance, and relationships.
You’ll learn:
Why retirement tax rates can look different from your working years
How even modest tax savings can compound, and where timing creates planning opportunities
Why lower taxes can be offset by other costs, and why the best moves strengthen relationships
Chapters
00:00 Don’t Let Taxes Choose Your Retirement State
02:13 Relationships Before Tax Rates (1)
05:46 Why Retirees Move States (2)
08:14 Cost of Living vs. Tax Rates
11:38 Retirement Income Tax Differences (3, 4)
14:27 Residency and Second Homes
18:27 Survivor Tax Penalty and Estate Taxes
23:04 Timing the Move and Planning Opportunities
31:35 The Costs That Offset Tax Savings
35:32 Quality of Life First, Money Second
Sources
Harvard Study of Adult Development, “Grant and Glueck Study.”https://www.adultdevelopmentstudy.org/grantandglueckstudy
SmartAsset, “Where Retirees Are Moving - 2025 Study.”https://smartasset.com/data-studies/where-retirees-move-2025
Fidelity, “The Best States to Retire for Taxes.”https://www.fidelity.com/learning-center/personal-finance/best-states-to-retire-for-taxes
Fidelity, “Is Social Security Income Taxed?”https://www.fidelity.com/learning-center/personal-finance/is-social-security-taxed
Related episodes
The Goal of Tax Planning is to Minimize Lifetime Taxeshttps://www.youtube.com/watch?v=4yqL1F5lCCI
Where Should Your Extra Savings Go? | The Decision Dividend #33https://www.youtube.com/watch?v=MeusOx0uNEU
Should You Sell or Borrow from Your Portfolio? | Return on Reason #30https://www.youtube.com/watch?v=FlhdhEhDx1I
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Disclaimer
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. While no single study can determine what is most important for every individual, this research illustrates that non-financial considerations can play an important role when evaluating retirement decisions.
 
* CFP Board owns the marks CFP®, CERTIFIED FINANCIAL PLANNER®, and CFP® (with plaque design) in the U.S.

A rental property can have been a great investment and still no longer be a great investment to keep. Deciding what to do next requires weighing not just the expected return, but the broader set of tax-efficient exit options available to real estate owners.
In Episode 37 of The Decision Dividend, we’re joined by Dan Mong, one of Greenspring’s most experienced advisors in real estate planning, to assess a property’s expected return and weigh the after-tax tradeoffs of selling, refinancing, or reinvesting.
You’ll learn:
How to periodically reassess a rental property’s investment performance using cap rate, return on equity, and its expected return relative to other opportunities
How capital gains, depreciation recapture, net investment income tax, and taxable “boot” can affect the after-tax outcome of a sale or exchange
How the main options work, including selling and reinvesting the proceeds, refinancing, completing a 1031 exchange, and investing through a Delaware Statutory Trust (DST)
Chapters
00:00 How to Exit a Rental Property Tax-Efficiently02:08 Should You Keep or Sell?11:24 The Tax Cost of Selling16:44 Sell, Reinvest, or Refinance23:29 How a 1031 Exchange Works32:02 When a 1031 Exchange Becomes Taxable35:20 Delaware Statutory Trusts45:40 Start With the End Goal
Related episode:Real Estate: Expected Returns and Expected Headaches | The Decision Dividend #9
Learn More About Dan Mong:https://greenspringadvisors.com/about/team/daniel-mong-cfp/
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Subscribe for Email Updates:https://greenspringadvisors.com/greenstream-podcast
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.

Can someone be a fiduciary while also earning commissions for selling financial products? The answer is more complicated than many investors realize.
In Episode 36 of The Decision Dividend, Pat Collins and Marcus Schafer explore the history and meaning of fiduciary duty, the different standards governing financial advice, and the signals investors can use to evaluate an advisor.
You’ll learn:
Why fiduciary duty requires the duty of loyalty and the duty of care.
How investment advisers, broker-dealers, hybrid advisors, and CFP professionals can operate under different standards and forms of oversight.
Why investors should evaluate compensation, registration, credentials, experience, and firm structure together rather than relying on a single label.
 
Sources
Douglas Harper, “Fiduciary,” Online Etymology Dictionary. https://www.etymonline.com/word/fiduciary
Irina Gvelesiani, “From the History of the Development of ‘Trust’ and Terminological Units Related to It,” Electronic International Interdisciplinary Conference, 2013. https://www.researchgate.net/publication/286912647_From_the_History_of_the_Development_of_Trust_and_Terminological_Units_Related_to_it
U.S. Securities and Exchange Commission, “Commission Interpretation Regarding Standard of Conduct for Investment Advisers,” Release No. IA-5248, 2019. https://www.federalregister.gov/d/2019-12208
U.S. Securities and Exchange Commission, “Regulation Best Interest: The Broker-Dealer Standard of Conduct,” Release No. 34-86031, 2019. https://www.sec.gov/rules-regulations/2019/06/s7-07-18
CFP Board, “Code of Ethics and Standards of Conduct.” https://www.cfp.net/ethics/code-of-ethics-and-standards-of-conduct
Electronic Code of Federal Regulations, 29 CFR § 2510.3-21, “Definition of Fiduciary.” https://www.ecfr.gov/current/title-29/subtitle-B/chapter-XXV/subchapter-B/part-2510/section-2510.3-21
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Subscribe for Email Updates: https://greenspringadvisors.com/greenstream-podcast
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.

Using SpaceX to understand IPO access, pricing, and expected returns.
SpaceX may be a high-profile company, and it is rare for a private company to go public at a valuation that would place it among the largest companies in the market.
In Episode 35 of The Decision Dividend, we use SpaceX to understand IPO access, pricing, and expected returns. We look at what history says about IPO returns and why the first-day “pop” is not always available to ordinary investors.
You’ll learn:
How the outside view changes the IPO question by asking who is selling, who is getting access, and what index funds may be forced to buy later.
What the historical evidence says about IPO pops, long-run returns, and low-float offerings.
Why the irony of diversified investing is that you may already have exposure to the economic benefits of companies like SpaceX, OpenAI, and Anthropic without chasing direct access.
 
Chapters:
00:00 Should You Chase the Next Big IPO?Using SpaceX to understand IPO access, pricing, and expected returns.
00:46 Decision vs. Outcome (1)How base rates and the outside view can help investors evaluate SpaceX, OpenAI, Anthropic, and the next big IPO.
03:04 SpaceX at a Mega-Cap ValuationWhy a remarkable business can still require extraordinary growth to justify an extraordinary price.
05:03 Limited Float, Lockups, and Hype (2, 3)How limited supply, insider lockups, and investor excitement can shape the early IPO experience.
07:53 IPO Waves and Market Timing (4, 5)Why companies may choose to go public when public-market prices, sentiment, and funding conditions are favorable.
09:42 How IPO Pricing Works (5, 6)The role of underwriters, roadshows, allocations, and the tension between what companies want and what investors want.
13:20 Who Captures the First-Day Pop? (2, 3, 5)Why the IPO “pop” is often measured from the offer price, not the price ordinary investors may actually pay.
22:15 What the IPO Evidence Shows (2, 3, 5)What decades of research suggest about first-day returns, longer-term returns, low-float offerings, and IPO characteristics.
28:30 How Diversified Investors Get Exposure (7)Why investors may already benefit through indirect ownership and public companies that finance, supply, and partner with the next big thing.
40:45 The Other Side of the Trade (1)Why employees, early investors, and concentrated shareholders may be trying to reduce risk at the same time public investors want to add it.
 
Sources:
Greenspring Advisors, “5 Tools for Better Decisions | The Decision Dividend #34.”https://www.youtube.com/watch?v=4WEK-1gMFd0
Jay R. Ritter, “IPO Data,” University of Florida.https://site.warrington.ufl.edu/ritter/ipo-data/
Dimensional, “What to Know About an IPO.”https://www.dimensional.com/us-en/insights/what-to-know-about-an-ipo
Luboš Pástor and Pietro Veronesi, “Stock Prices and IPO Waves,” NBER.https://www.nber.org/papers/w9858
Jay R. Ritter and Ivo Welch, “A Review of IPO Activity, Pricing, and Allocations,” NBER.https://www.nber.org/papers/w8805
Wall Street Journal, “SpaceX Is Aiming for Civilization on Mars. Its IPO Couldn’t Be More Old School.”https://www.wsj.com/finance/stocks/spacex-ipo-process-preparation-69f97465
Dimensional, “Hiding in Plain Sight: Private Asset Exposure Through Public Equities.”https://www.dimensional.com/us-en/insights/hiding-in-plain-sight-private-asset-exposure-through-public-equities
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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.
References to SpaceX, OpenAI, Anthropic, and IPOs are for educational purposes only and should not be construed as a recommendation to buy, sell, or hold any security, participate in any IPO, or invest in any private company. IPOs and private company investments involve unique risks, including limited information, valuation uncertainty, liquidity constraints, allocation limitations, volatility, and the potential loss of principal. Historical IPO data and examples may not be indicative of future results.

Practical frameworks for separating process from outcome. A good outcome can make a bad decision look smart. A bad outcome can make a good decision look foolish.
In Episode 34 of The Decision Dividend, we look at how to separate the quality of your decision from the luck of the result. To do that, we walk through five practical tools for making better decisions before, during, and after uncertainty shows up.
You’ll learn:
How a decision memo can help you judge your process without being fooled by the outcome
Why scorecards and base rates can make tradeoffs clearer and forecasts more realistic
How if-then rules and defaults can help turn better decisions into repeatable behavior
 
Chapters
00:00 5 Tools for Better DecisionsHow to separate the quality of a decision from the luck of the result.
01:11 Trust the EvidenceWhy better decisions start with process, data, science, and evidence.
02:00 When a Decision Needs a FrameworkHow to decide when a choice deserves structure and when an incremental step is enough.
03:48 Why Gut Instinct Can Mislead InvestorsHow the same instincts that helped humans avoid danger can hurt decision-making under uncertainty.
05:59 The Five Decision ToolsDecision memos, scorecards, base rates, if-then rules, and defaults.
06:48 Decision Memos and Journals (1)Why writing down your reasoning in advance can help you audit decisions later.
09:12 Scorecards and Tradeoffs (2)How a one-page scorecard can make tradeoffs clearer when there is no single right answer.
12:16 Base Rates (3, 8)Why the first question should be what usually happens in similar situations.
15:35 If-Then Rules and Guardrails (4)How pre-deciding your trigger and response can reduce improvisation under stress.
18:36 Defaults and Precommitment (5, 6, 7)Why making a decision once can be more effective than re-deciding every month.
21:48 Decision vs. Outcome (1)Why a bad decision can be rewarded by luck and a good decision can still disappoint.
26:33 The Decision 2x2 (1)A practical way to separate good and bad decisions from good and bad outcomes.
30:02 When Several Things Matter (2)How weighing multiple criteria can help compare financial and life decisions.
34:56 The Outside View (3, 10)Why personal experience can distort expectations for returns, risk, and future outcomes.
40:34 Learning from Wins and Losses (1,9)Why early success can create overconfidence, and why bad outcomes can sometimes teach useful lessons.
42:49 Win or LearnHow better decision-making compounds when you review the process, not just the result.
 
Sources
Jonathan Baron and John C. Hershey, “Outcome Bias in Decision Evaluation,” Journal of Personality and Social Psychology, 1988.https://bear.warrington.ufl.edu/brenner/mar7588/Papers/baron-hershey-jpsp1988.pdf
Samuel D. Bond, Kurt A. Carlson, and Ralph L. Keeney, “Generating Objectives: Can Decision Makers Articulate What They Want?,” Management Science, 2008.https://pubsonline.informs.org/doi/10.1287/mnsc.1070.0754
Roger Buehler, Dale Griffin, and Michael Ross, “Exploring the ‘Planning Fallacy’: Why People Underestimate Their Task Completion Times,” Journal of Personality and Social Psychology, 1994.https://web.mit.edu/curhan/www/docs/Articles/biases/67_J_Personality_and_Social_Psychology_366%2C_1994.pdf
Peter M. Gollwitzer and Paschal Sheeran, “Implementation Intentions and Goal Achievement: A Meta-Analysis of Effects and Processes,” Advances in Experimental Social Psychology, 2006.https://www.researchgate.net/publication/37367696_Implementation_Intentions_and_Goal_Achievement_A_Meta-Analysis_of_Effects_and_Processes
Brigitte C. Madrian and Dennis F. Shea, “The Power of Suggestion: Inertia in 401(k) Participation and Savings Behavior,” NBER Working Paper, 2000.https://www.nber.org/system/files/working_papers/w7682/w7682.pdf
Richard H. Thaler and Shlomo Benartzi, “Save More Tomorrow: Using Behavioral Economics to Increase Employee Saving,” Journal of Political Economy, 2004.https://www.anderson.ucla.edu/documents/areas/fac/accounting/smartjpe226.pdf
Sheena S. Iyengar, Gur Huberman, and Wei Jiang, “How Much Choice Is Too Much? Contributions to 401(k) Retirement Plans,” Pension Research Council Working Paper, 2003.https://pensionresearchcouncil.wharton.upenn.edu/publications/papers-2018/how-much-choice-is-too-much-contributions-to-401k-retirement-plans/
Jay R. Ritter, “The Long-Run Performance of Initial Public Offerings,” Journal of Finance, 1991.https://site.warrington.ufl.edu/ritter/files/The-Long-Run-Performance-of-Initial-Public-Offerings-1991-03.pdf
Hendrik Bessembinder, “Do Stocks Outperform Treasury Bills?,” Journal of Financial Economics, 2018.https://papers.ssrn.com/sol3/papers.cfm?abstract_id=2900447
UBS, “Global Investment Returns Yearbook 2026.”https://www.ubs.com/global/en/investment-bank/insights-and-data/articles/global-investment-returns-yearbook-2026.html
 
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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.

A research-informed order of operations for cash reserves, debt, retirement accounts, brokerage accounts, 529s, and mortgage prepayment.
The hard part of having extra savings is rarely finding a good option. It’s choosing between several.
In Episode 33 of The Decision Dividend, Pat Collins and Marcus Schafer walk through a practical order of operations to decide where your extra savings should go. The answer is not always the account with the best theoretical return. The right sequence depends on cash flow, liquidity, taxes, debt, goals, and behavior.
You’ll learn:
How to avoid the high-income paycheck-to-paycheck trap by setting a savings target before lifestyle absorbs the next raise
Which dollars often deserve early consideration: emergency cash, high-interest debt, and employer-provided matching opportunities
What research says about the harder tradeoffs, including Roth vs. pre-tax, taxable brokerage vs. 529s, and extra mortgage payments vs. investing
Chapters
00:00 Where Should Your Extra Savings Go?Why the next-dollar decision is really a tradeoff between several good options.
01:34 Tightwads, Spendthrifts, and the Pain of Paying (1)How different people experience spending and saving differently, and why behavior matters before optimization.
02:40 Savings Rate Comes First (2)Why the most powerful planning variable is often not Roth vs. pre-tax, but whether lifestyle absorbs the next raise.
07:09 Make the Plan Automatic (3, 4, 5)Why defaults, payroll deductions, and automation often matter more than a perfectly designed spreadsheet.
13:35 The Savings WaterfallA practical starting point: create margin, build emergency reserves, avoid high-interest debt, and capture employer-provided matching opportunities.
16:40 Liquidity, Taxes, and Account FlexibilityWhy the same dollar feels different in cash, taxable brokerage, pre-tax retirement accounts, and Roth accounts.
20:26 Taxable Brokerage vs. Retirement AccountsHow tax drag, liquidity, goal timing, and future uncertainty shape where the next dollar should go.
28:00 Roth vs. Pre-Tax Is Not a Religion (6, 7)Age + 20% is a good rule of thumb but current tax rates, future tax rates, tax uncertainty, and account access make this decision highly personal.
31:20 Mortgage Prepayment vs. Investing (8)How to compare the guaranteed return of paying down debt against the double tax and return benefits of retirement investing.
38:59 The Theory Only Works If You Actually Do It (3, 4, 5, 8)Why behavior can erase the benefits of a more optimal strategy if the money never actually gets invested.
43:10 College Savings, 529s, and Optionality (9)Why education funding should be balanced against retirement, flexibility, and uncertainty about future college costs.
52:48 Build a Repeatable SystemWhy rules of thumb can help, but personalized advice matters when cash flow, taxes, debt, goals, and behavior collide.
Sources
Scott I. Rick, Cynthia E. Cryder, and George Loewenstein, “Tightwads and Spendthrifts,” Journal of Consumer Research, 2008. https://academic.oup.com/jcr/article-abstract/34/6/767/1795103
Goldman Sachs Asset Management, Retirement Survey & Insights Report 2025. https://am.gs.com/en-us/advisors/insights/report-survey/retirement-survey
Brigitte C. Madrian and Dennis F. Shea, “The Power of Suggestion: Inertia in 401(k) Participation and Savings Behavior.” https://www.nber.org/system/files/working_papers/w7682/w7682.pdf
Richard H. Thaler and Shlomo Benartzi, “Save More Tomorrow: Using Behavioral Economics to Increase Employee Saving.” https://www.anderson.ucla.edu/documents/areas/fac/accounting/smartjpe226.pdf
Raj Chetty, John N. Friedman, Søren Leth-Petersen, Torben Heien Nielsen, and Tore Olsen, “Active vs. Passive Decisions and Crowd-Out in Retirement Savings Accounts.” https://eml.berkeley.edu/~saez/course/chettyatQJE14savings.pdf
David C. Brown, Scott Cederburg, and Michael S. O’Doherty, “Tax Uncertainty and Retirement Savings Diversification.” https://www.sciencedirect.com/science/article/pii/S0304405X17302519
Wall Street Journal, “Why So Many People Get Financial Advice That Is Wrong for Them.” https://www.wsj.com/finance/investing/financial-advice-investments-personalization-fea73e95
Gene Amromin, Jennifer Huang, and Clemens Sialm, “The Tradeoff Between Mortgage Prepayments and Tax-Deferred Retirement Savings.” https://www.nber.org/papers/w12502
Fidelity, “Understanding 529 Rollovers to a Roth IRA.” https://www.fidelity.com/learning-center/personal-finance/529-rollover-to-roth
 
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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.

Too often, families spend more time planning how to build wealth than how to pass it on. In Episode 32, we’re joined by Ron Diamond* to discuss family governance, inheritance, and how to prepare the next generation for wealth without creating confusion, conflict, or entitlement.
You’ll learn:
Why investing should often come after governance, values, and family communication
How to prepare children for wealth without creating entitlement
What families should address before a liquidity event or inheritance
 
About Ron DiamondWe asked Ron to join us because he has spent years working with families and family offices on exactly these family governance challenges. He is Founder and Chairman of Diamond Wealth, a leader in the family office community through TIGER 21, and a member of the Advisory Board and Steering Committee for the University of Chicago Booth School of Business Family Office Initiative.
https://www.linkedin.com/in/ronalddiamond/
https://www.chicagobooth.edu/research/family-office-initiative
 
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
 
*Guest speakers featured are independent third parties and are not affiliated with Greenspring. No cash or non-cash compensation was provided to or received by Greenspring in connection with any guest appearance. The views and opinions expressed by guests are their own as of the date of recording and do not necessarily reflect the views of Greenspring. Appearance on the podcast should not be construed as an endorsement of Greenspring.
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.

We revisit a question we expect to ask every 1-2 years. Is this time different? The catalyst this time is energy and trade shocks tied to conflict. You’ll learn:
How common market drops like this are and how often they rebound
How separating your roles as a citizen, consumer, and investor can guide what action, if any, to take
What history tells us about market returns through past conflicts and energy shocks
The questions investors are asking and how we think about what to do
For additional context and visuals shown in the episode, you can subscribe to Justin Brown’s Chart of the Week.
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) Tariffs: Is This Time Different? | #6 (Greenspring Advisors, 2025)
(2) Do Large Oil Price Moves Impact Future Market Returns? (Greenspring Advisors, 2026)
(3) U.S. Market Returns After Major Conflicts (Greenspring Advisors, 2026)
 
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.