Return on Reason

Return on Reason

A podcast specifically focused on helping every person live their ideal life by helping them make better decisions around their finances, relationships, and life.

Episodes

April 28, 2026 49 mins

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 e...
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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 inv...
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Many investors assume that if they need cash, even for short-term expenses, they have one option: sell their investments. In Episode 30 of Return on Reason, we discuss a less widely understood option, borrowing against your investment portfolio. It may be one option for accessing short-term liquidity, but it also introduces tradeoffs that stretch beyond the interest rate. You’ll learn:

  • Four ways to access cash from your port...
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March 17, 2026 50 mins

Cash feels safe. Over time, excess cash quietly works against you through lower returns, inflation, and taxes.

In Episode 29 of Return on Reason, we dive into how to optimize the return on your cash by exploring how much to hold and where to hold it, so that it works for you, not for your bank or brokerage.

  • When cash may stop being a reserve and become a drag on wealth
  • Why it’s easier than ever to earn more on cash and how sma...
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March 3, 2026 50 mins

AI, banking innovation, estate planning tools. Why better tools don’t automatically mean better decisions.

Innovation in personal finance is no longer constrained to investments. Access to new tools is expanding. But better information does not eliminate trade-offs.

In Episode 28 of Return on Reason (formerly Greenstream), we explore where innovation genuinely adds value and where judgment, coordination, and incentives still determ...

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February 17, 2026 51 mins

After-tax outcomes. Concentrated wealth. Private market access. The math matters more than the marketing. Innovation is inevitable. Access to new investment tools continues to expand. The question is whether the benefits outweigh the costs.

In Episode 27 of Greenstream, we discuss the tradeoffs behind strategies designed to improve after-tax outcomes, manage concentrated wealth, and pursue private market opportunities to determine ...

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February 3, 2026 51 mins

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 guaranteed
  • Why stocks vs. bonds is the original (and one of the biggest) factors bet investors make
  • How factor investing hel...
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January 20, 2026 48 mins

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 Epis...

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 do...

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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.
  • ...
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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, toleranc...
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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 ca...
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November 6, 2025 49 mins

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 po...
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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 compli...
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Board service is one of the most impactful ways to shape organizations, give back, and expand your influence. In this episode, Lindsay Jordan and Robyn Bew, board governance experts from EY (sharing personal perspectives), unpack what boards do, why they matter for every organization, and how you can position yourself to join one.

 

Sources

EY Center for Board Matters – Our latest thinking | EY - US https://www.ey.com/en_us/board-m...

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Are you investing or are you gambling? In episode 17 of Greenstream, we unpack evidence from casinos, sportsbooks, and academic finance to show how the odds work against gamblers but for investors. You’ll learn about:

  • Why time is an investor’s ally but gambler’s enemy
  • How the “favorite–longshot bias” from horse racing shows up in lottery stocks and IPOs
  • Four practical ways to help stack the odds in your favor and invest like t...
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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:

  • What we believe to be biases and how they manifest themselves in port...
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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:

  • What different types of risk matter: catastrophic, opportunity cost, and missed goals
  • Why individual stocks are riskier than you might t...
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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 investme...

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August 1, 2025 78 mins

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.onmicrosof...

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