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PODCAST · business

Mailbox Money

by Jackson Wood

You Guide through Safe, Sacred, and Speculative investing with a plan and a purpose to do more good with new found peace of mind.

Publisher-supplied feed metadata · PodParley refreshed Mar 14, 2026 · Source feed

Episodes

  1. The Return of the Dividend

    In this episode we talk about the return of dividends! We've seen some new surprising companies start paying dividends recently and we think talking through this decision can help investors understand where dividends belong in a portfolio. To schedule a meeting with our team, email us:...

  2. Grand Slams

    In this episode we talk about sports and math and the intersection of both. In any investment we make, we care more about the direction of the moat rather than the size of the moat itself. One of the best examples we have of this is Dicks Sporting Goods. To listen to our previous episode on this...

  3. Bitcoin!

    In this episode we talk about Bitcoin. We are incredibly proud of our longstanding belief in Bitcoin and we discuss recent changes in the landscape and how we frame Bitcoin inside of our portfolio. To learn more, or to schedule a meeting with our team, email us: [email protected]...

  4. Mikan Drill for Stocks

    The arc of complex data analysis surrounding any question now is expanding so fast that we wonder if investors are ending up farther away from the most efficient goal – a simple and repeatable solution Are we talking basketball or stocks? YES!!! Join our bracket pool here:...

  5. Schmuck Insurance

    In this episode we discuss something that we've recently changed our mind on, and something that's blown our minds. So, what is Schmuck Insurance?! We hope you enjoy this episode. To schedule a meeting with our team, email us: [email protected] www.freedomdaysolutions.com

  6. Yield on Cost - The Secret Sauce

    In this episode we give specific examples of Yield on Cost and how powerful it can be for your portfolio - and peace of mind. Often times investors find themselves searching for high yielding companies while ignoring those with a lower yield. Dividend growth investing can provide a growing stream...

  7. Benchmarking: Useful or Not?

    In this episode we discuss benchmarking. Many investors are confused. There are thousands of different indexes and benchmarks used by Wall Street. Instead of creating confusion, performance chasing, and potentially causing yourself problems, what if you benchmarked to Peace of Mind? To schedule a...

  8. Parenting Pow Wow

    In this episode we share 5 lessons we have learned to sprinkle the magic of investing across 5 kids (each!). To schedule a meeting with our team, email us: [email protected] www.freedomdaysolutions.com

  9. The Most Underrated Question for Investors

    In this episode Ryan and Jackson discuss the most underrated question for investors: "When can I get my money back?" Liquidity is undervalued by too many. Those who understand its upside will tell you it's worth more than most features described on investment products. In today's episode, we're...

  10. Why Dividend Growth?

    We're back! First off, we wanted to thank everyone that reached out during our hiatus. It means a lot to us that we have such thoughtful listeners and it felt good to read your messages. In today's episode we go right at Wall Street and discuss our Holy Grail of Investing: Dividend Growth. We...

  11. Lessons from Charlie Munger

    Jackson goes solo and shares incredible investing (and life) lessons from the late Charlie Munger. Charlie Munger passed away in November 2023 at the helm of Berkshire Hathaway. Not only was Charlie an incredibly wise investor, he was a great person and we are fortunate to be able to learn from…

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  12. Chasing What Matters

    This week we wanted to share a wonderful podcast Ryan had the honor of being on, Chasing What Matters. The Chasing What Matters podcast is hosted by Glenn and Jacob Robinson (father and son) and brings you interviews with industry shaping leaders from all walks of life to discuss their leadership...

  13. Wait for the Train

    In this episode we discuss performance chasing versus sticking to an evidence based investment strategy designed to help you reach your goals. We cite a study from Vanguard about the outperformance of sticking with a specific strategy compared to performance chasing and how you can reach your...

  14. Grateful for Simplest Recipies

    We all have a lot to be grateful for. In today's episode we discuss some of the many things we appreciate. We are grateful for you listening to our show! www.freedomdaysolutions.com

  15. $70 Million to Charity

    In this episode we talk about the incredible story of Theodore R. Johnson. Mr. Johnson never made more than $14,000 a year, but he invested wisely so wisely that he made $70 million by the time he was 90 in 1991.

  16. Wildly Simple Stock Math

    Today we are going to share one of the most incredible stories we’ve been lucky to learn from, born from the simplest of all stock market math – do you have debt or cash? This company is another example of why we believe in actively managing two different stock portfolios. The backbone for...

  17. The Price You Pay

    In this episode we look at a time period, 13 years to be exact, where the market returned a total of -2.97%. Now this isn’t a prediction of what we will see for this decade, but it proves a valuable lesson for all investors, especially those willing to pop the hood and dive in a little deeper.

  18. Bank Yourself

    We recently saw and advertisement in the Wall Street Journal, for a “special CD rate of 6%.” It took us reading the footnotes to discover the truth. In this episode we discuss Bank Yourself, our version of earning an attractive rate on Safe Money, cutting out all the middlemen and doing exactly...

  19. Unapologetic Upside

    In this episode we discuss the uncommon upside found in capitalism and how it can benefit those most in need. We also discuss Donor Advised Funds and how they can play an incredible part in your own financial plan. To schedule a meeting with our team, email us at [email protected]

  20. Water on Fire

    In this episode we discuss a valuable lesson we learned while in Chicago. We discuss one of our opportunities, why we believe it’s an uncrowded and overlooked company and share some of the math behind our research. To learn more, email us: [email protected] www.freedomdaysolutions.com

  21. The Exciting State of Cryptocurrency

    One of the unfortunate aspects of speculation is that price often drives narrative. Nowhere is this more obvious that in cryptocurrency and crypto assets. I’ve been investing and involved in crypto since 2012. Since then, we’ve seen 3 very large “super cycles” in crypto. As the price goes up…

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  22. Electrifying Growth or Value?

    One of our humblest but largest disagreements with most investment professionals is that Growth OR Value is the wrong question. Why not be selective enough to wait for BOTH?! Today, we’ll share a specific example that is one of our favorites overlooked and misunderstood industries that we believe...

  23. How Do You Know When to Sell?

    Peter Lynch once said, “Behind every stock is a company. Find out what it’s doing.” For every investor and their investment journey, there ultimately comes a time when one of their holdings experiences some sort of trouble. It really doesn’t matter how much research you’ve done, or how convicted...

  24. What is Freedom Day?

    In this episode we discuss Freedom Day. In the midst of complex retirement planning strategies, often designed to enrich Wall Street, we explain our process and share what goes into building a Freedom Day plan. We believe that when you have multiple streams of income, that grow above the rate of...

  25. 5-Tool Prospects

    In this episode we discuss the disciplines and freedoms of active management. When grounded in evidence-based data, we find ourselves far away from the crowds of predictions and anxiety. Today we’re going to take you into one of our Stock Tournaments: the 5-Tool Prospects! To schedule a meeting...

  26. Bank Yourself

    Bank deposits have hit an all-time high with $10.7 Trillion sitting in checking and savings accounts. With rates having gone up significantly the last two years and the average U.S bank savings rate only yielding 0.07%, it’s vitally important that investors know how to “bank themselves.” Email…

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  27. An Ounce of Optimism, a Pound of Prudence

    Cash is yielding more now that it has in a long time. A lot of investors are flocking to cash as the current market and economy is scaring them. In this episode we discuss the historical opportunities seen after money market rated peaked and the outperformance, over time, of a dividend growth...

  28. Truth Serum

    In crunching through a couple thousand tickers in our Stock Tournaments this weekend, and then in looking one by one at about a hundred different price charts, we were compelled to share some Grace and Peace of Mind to anybody wondering what the heck is going on. We want this podcast to always be...

  29. Thinking Like a Business Owner

    As dividend growth investors, our goal is to generate a rising stream of sustainable dividend income, through careful investment in quality dividend growth stocks. Our investment plans are not dependent on market fluctuations. In fact, even if they closed the market tomorrow, I don’t think it…

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  30. Consumer InDiscretion

    Today we’re going to look inside one sector of the stock market with two of the wildest facts we’ve ever found. As we look at consumer discretionary businesses, we realize the opportunity offered as part of our Speculative sleeve of investment portfolios. To schedule a meeting with our team…

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  31. What About Cash?

    In this episode we talk about cash. We go over where it belongs in a portfolio, how much we hold, and how to think about cash inside of your investment account. We discuss our Simple Portfolio: Safe Money Sacred Money Speculative Money To schedule a meeting with our team, reach out by emailing:...

  32. Road Trips!

    In todays show, we go over some investment ideas we learned about during recent road trips with kids. As we drove around the country we connected the dots from our research in the office to hands-on unique and uncrowded opportunities. To schedule a meeting with our team, email us:...

  33. An Electric Canary in Clean Energy Mine

    In this episode we discuss a sizzling opportunity we came across in one of the most important commodities that isn’t well understood - electricity. We talk through the shift from coal fired power to a nation and world of clean energy, and what it takes to get there.

  34. It's A Small World

    In today's episode we want to celebrate small business and business owners. We discuss a subscriber question from Greg: "I trust you with my treasure, so I can decide where my time and talents go. You left a large firm and started over again with nothing. What was that struggle like, because I...

  35. Where to Hide

    Title: Where to Hide In this episode we discuss recency bias. How it’s seen in a simple game of Hide and Seek with your kids and especially in markets and investing. When markets get tough, the gurus come out in full force claiming that they know where to allocate funds better than others. We...

  36. Stock Market's Neighborhood Report

    In this episode we discuss our approach to technical analysis. Not only do we pop the hood and do bottom up fundamental analysis, we also look at the top down technical analysis of each stock and sector. We discuss the reasoning behind looking at both fundamentals and technicals, share examples…

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  37. Happy Graduation DayS

    In this episode Ryan shares the notes he’s taken especially for his graduating senior. He shares 4 quarters of advice: Dare to be Different Work Life IMbalance What it Means to Be a Real Man: LIFT TRUST in Time If you liked this episode, we’d greatly appreciate it if you left a review and shared...

  38. Things to Teach Young Kids about Money

    In this episode we talk about the certain values we try to teach our kids about money. 1. The Value of Money 2. Saving Money 3. Debt can be a tool, or a weapon of mass destruction 4. Invest WITH your kids 5. Aaron Watson’s life advice 6. The Power of Compounding We referenced this earlier…

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  39. Raises & Reasons

    We recorded this on May 5th, which was the two year anniversary of our dividend growth fund. Central to our strategy is owning companies that increase their dividend, which ultimately results in growing income for stakeholders. In this episode we discuss: • The Banking Crisis (revealing who the...

  40. Personal Pensions

    In this episode we talk about the original Mailbox Money. We go all the way back to 1850 when American Express established the first private pension plan in the United States. In 1978 Ted Benna discovered a small paragraph “k” in IRS code “401” which allowed employers a tax break for allowing…

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  41. What's happening to Crypto?

    In this episode we discuss one of our Speculative Investments: Cryptocurrency The last year has been a rollercoaster for crypto. We've been bombarded by bad news, negative headlines, and a seemingly endless supply of negativity from the crypto space. Yet, the coins themselves tell a different...

  42. Building a Roster of Stocks

    There is a lot of confusion in the world of investing. As investors we are constantly inundated and asked to pick a single investment strategy from the very beginning. Growth or Value Investing Cyclicals or Secular Cash Flow or Compounders Silicon Valley or Permian Basin Small Cap or Large Cap...

  43. The Power of Dividend Growth

    In this episode we discuss the power of dividend growth investing. We discuss the simple operating system we learn from Warren Buffet, talk about active management in investing, and go through the math behind dividend growth. To schedule a meeting with our team, email us:...

  44. How Safe is Your Safe Money?

    The last few weeks have been pretty eventful in the markets. All of the sudden, everyone is wondering "Is my safe money really that safe?" In this episode we pull back the curtain on Safe Money and discuss 5 simple concepts that will help you understand how to allocate your Safe Money, so that it...

  45. A Crypto Discussion with Nate Geraci

    In this episode we have special guest, Nate Geraci, on the show to discuss crypto and the Grayscale Bitcoin Trust (GBTC). Our firm offers Freedom Day Crypto Assets, an actively managed crypto strategy with direct ownership of cryptocurrency and all of the intrinsic benefits of the asset class....

  46. Competition’s Special Dividend

    In this episode we dive into our simple and repeatable process that allows us to understand what is happening in the markets. Ryan tells the incredible story of and incredible entrepreneur that has resulted in $332 Million of dividends being paid to stakeholders this year and a $12 Billion dollar...

  47. The Siren Song of Investing

    In this episode we pull out some classical literature, specifically Homer's Iliad. We talk about the story of Odysseus, and the Song of The Sirens. I promise it relates to investing! We discuss: Looking at dividends over market prices Problems with the 4% Rule Emotional benefits of focusing on...

  48. Globetrotter Investing

    In this episode we talk about international investing. Ryan shares a great story that made him think about the benefits of investing over seas. We go through some compelling math that we see popping up in international markets. We talk about two strategies we use, in our personal accounts, and…

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  49. Dividends: Holy Grail or Worthless Distraction?

    ***to view the charts: https://youtu.be/xPr4_m7WkGE In this episode we talk all about dividends. We dive into: - Market volatility viewed through the lens of dividends - Stakeholder vs. trader mentality - Why a company may or may not pay a dividend ...and much more!...

  50. Your IRR

    In this episode we discuss IRR. Inspired by a dear friend, we talk about changing the definition of Internal Rate of Return (IRR), into something more important and more long-lasting. Who is measuring our true internal satisfaction with an investment? Your IRR: It's Real & Repeatable...

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ABOUT THIS SHOW

You Guide through Safe, Sacred, and Speculative investing with a plan and a purpose to do more good with new found peace of mind.

HOSTED BY

Jackson Wood

CATEGORIES

Frequently Asked Questions

How many episodes does Mailbox Money have?

Mailbox Money currently has 102 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is Mailbox Money about?

You Guide through Safe, Sacred, and Speculative investing with a plan and a purpose to do more good with new found peace of mind.

How often does Mailbox Money release new episodes?

Mailbox Money publishes regularly with 102 episodes available. Check the episode list for the typical release schedule.

Where can I listen to Mailbox Money?

You can listen to Mailbox Money on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.

Who hosts Mailbox Money?

Mailbox Money is created and hosted by Jackson Wood.
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