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Smart Investing with Brent & Chase Wilsey

Smart Investing with Brent & Chase Wilsey

Auteur(s): Brent and Chase Wilsey
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Smart Investing is the radio show where Brent and Chase try to make investing easier to understand. They demonstrate long-term investment strategies to help you find good value investments.Brent and Chase Wilsey Finances personnelles Économie
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  • December 12th, 2025 | Copyright Lawsuit against AI company Perplexity, Apple’s Management Drain, It’s time for commercial property into your portfolio, The Benefits of Capital Gain Harvesting & More
    Dec 13 2025

    Another lawsuit against generative AI company Perplexity for copyright infringement

    The New York Times has had enough, and they have filed a lawsuit in a New York Federal court. In October 2024, the Times sent a notice to stop accessing and using their content and then followed up with another notice this past July. Perplexity continues to ignore the warnings and a spokesperson for the company, Jesse Dwyer, said publishers have been suing new tech companies for a hundred years starting with radio, TV, the Internet and social media, but that has never worked out for them. I think this is a little bit different since AI pretty much takes the content directly from the…


    Just when Apple corrected their major problems, it looks like there’s a management drain

    Apple did a great job handling the proposed tariffs on its products, which would have devastated the company. Also, in court they managed to keep the $20 billion a year they receive from Google. But now, they seem to be fighting a management exit by some of their top executives. Over the last couple of weeks, it was announced that both their General Council and Head of Policy will be retiring next year. Another major concern was also announced in that timeframe that their Head of Artificial Intelligence and Strategy is also going to retire. Making matters worse, their Chief Operating Officer said he’ll be retiring in July of next year. Don’t worry about CEO Tim Cook being age 65, he said he is not considering retirement, and people at the company said he is not slowing down at all. It was also recently announced that Meta…


    It’s time to put some commercial property into your portfolio

    You may be questioning why would I put real estate like commercial property in my portfolio that over the last five years or so has had a return of maybe 7% versus stocks that have done much better? The simple answer is the basic investing principle of buying low and selling high. Looking forward, I believe commercial real estate over the next five years should get better returns than artificial intelligence considering the fact that it is very pricey. Data from MSCI revealed that year to date large investors have purchased $4.6 billion more US commercial property than they sold. That is the first time that has happened in three years, and deal activity is still low compared to history. US commercial real estate values are off from the peak in 2022 and are now down on average around 17%. Looking just at commercial offices, there is a better…


    Financial Planning: The Benefits of Capital Gain Harvesting

    While many investors focus on tax-loss harvesting, harvesting capital gains can be just as valuable especially when you fall into the 0% long-term capital gains bracket. For example, in 2025 a married couple filing jointly can have taxable income up to $96,700 and still pay 0% on long-term gains. Because the standard deduction ranges from $31,500 to $46,700, and itemized deductions can be even larger, a household’s total gross income can potentially exceed $150,000 while still remaining in the 0% capital gains bracket. If an investor wants to keep…


    Companies Discussed: The Brink's Company (BCO), PVH Corp. (PVH), Pure Storage, Inc. (PSTG) & The Kroger Co. (KR)

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    56 min
  • December 5th, 2025 | Why does the AI revolution scare us? Bitcoin holder Strategy, Holiday shopping hits record levels! When Tax-Loss Harvesting Makes Sense and When It Doesn’t & More
    Dec 6 2025

    We have gone through four industrial revolutions in the US, why does the AI revolution scare us the most?

    Industrial revolutions are nothing new in the United States as we have had four including the current one we are in. The first one came in the mid-18th century when changes came for waterpower, steam engines, and textile manufacturing. The second industrial revolution was in the mid-19th century when steel became a big factor along with electricity and mass production. We also saw transportation…


    Bitcoin holder Strategy should be getting nervous about the price of Bitcoin

    The public company Strategy, which used to be known as MicroStrategy and trades under the symbol MSTR, should be getting nervous about its 650,000 Bitcoins that are worth around $56 billion depending on the day. The problem is the company has about $8 billion of convertible bonds outstanding that require interest payments and about $7.6 billion of perpetual preferred stock that also pays dividends. The cost to pay the interest and these dividends is about $780 million annually and since all the company’s assets are essentially in Bitcoin, they don’t receive any interest or profits from that…


    Holiday shopping hits record levels!

    We continue to see conflicting data when it comes to the health of the consumer. They continue to say they don't feel good, but the hard data and the actual numbers remain quite strong. In a positive note from the National Retail Federation (NRF), an estimated 202.9 million consumers shopped during the five-day stretch from Thanksgiving Day through Cyber Monday. That is the largest turnout since data for the five-day period started being collected in 2017, and it easily tops last year's level of 197 million shoppers. Expectations for the period were also quite low considering the estimate was for just 186.9 million shoppers. While online shoppers increased 9% year over year to 134.9 million people, in-store shoppers still saw a nice increase of 3% to 129.5 million people. Adobe also provided sales data for the five-day period that indicated consumers spent $44.2 billion online, which was a 7.7% year-over-year jump. Black Friday in particular…


    Financial Planning: When Tax-Loss Harvesting Makes Sense and When It Doesn’t

    Tax-loss harvesting is often promoted as a smart tax-saving strategy, but investors should understand its pitfalls before hitting the sell button. Selling a position at a loss may reduce taxes today, but it could also mean missing a rebound in that investment potentially costing more in lost gains than the tax benefit received. For example, if an investor buys a stock for $50,000 and harvests a $5,000 loss when the investment drops to $45,000, and they are in a 24.3% combined tax bracket (15% federal + 9.3% state), the tax savings is just over $1,200. That means the investment only needs to rise 2.7% to wipe out the benefit of harvesting, something that could easily occur during the required 30-day wash-sale waiting period. Even if the position doesn’t rebound, repurchasing after 31 days locks in a lower cost basis, potentially increasing future taxable gains possibly in a higher tax bracket. Many investors…


    Companies Discussed: Weyerhaeuser Company (WY), Netflix, Inc. (NFLX), Energizer Holdings, Inc. (ENR) & Valvoline Inc. (VVV)

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    56 min
  • November 21st, 2025 | Fast food like Wendy’s experiencing a slowdown, Home Affordability hits a 50-year low, Robinhood looks more like gambling than investing, Employer Coverage vs. Medicare & More
    Nov 22 2025

    Fast food restaurants like Wendy’s are experiencing a slowdown in business

    The fast-food restaurant Wendy’s is planning on closing hundreds of locations throughout next year because they continue to see a slowdown in spending from their customers. They said most of their low-income consumers are cutting spending and making fewer trips with smaller purchases at the restaurants. Wendy’s increased prices after the pandemic at a higher rate than grocery stores and now other fast-food restaurants have begun to add value menus to keep customers coming back, but Wendy’s has held firm and not created any values for their…


    The affordability index for people buying a home is the worst in 50 years

    People may be excited about buying a home because mortgage rates are around the lowest they’ve been in over a year, but the affordability of a home is still far out of reach for many. The reason for this, and we have talked about this for the last few years, is that the increase in the price of homes has far outpaced the increase in people’s income. The 50-year average for a price-to-income ratio is around four times, and it reached a low in 1999 of around 3.6 times. But with the rapid increase of homes over the last few years, the price to income ratio has climbed to slightly over five times. Also not helping are the increases in home insurance costs and property taxes. Back in the summer of…


    The brokerage firm Robinhood looks more like a gambling platform than a brokerage firm

    Robinhood initially went public at $38 a share in 2023 and the stock then fell to under $10 a share. It has recovered nicely since then as it’s now trading around $110 a share. What has caused this shift and the huge increase in the stock price? One big reason is that the company has really allowed major speculation for their investors. Starting off with crypto, they have allowed people to buy coins like BONK, Dogwifhat and Pudgy Penguins. Just when you think there’s no way they could come up with anything more speculative, surprise; they have come up with an investment known as prediction markets and event trading. Somehow the regulators have let this slide or maybe since government agencies don’t move that quickly, it just has not been addressed yet. It appears for investors on their app that you can predict what the outcome will be of a football game, politics, contracts over economics, even if aliens…


    Financial Planning: The Real Cost of Employer Coverage vs. Medicare

    When reaching age 65, sometimes there is the option to join Medicare or stay with an employer health insurance plan. This is most common when a spouse retires after age 65 and they have the ability to join their spouse’s work plan. When comparing the cost of coverage, there is a key difference in how each affects your tax bill. Premiums paid through payroll for employer-sponsored health insurance are pre-tax, meaning you avoid federal, state, and payroll taxes such as the 6.2% Social Security, 1.45% Medicare, and 1.2% CA SDI tax in California. This is different from a 401(k) for example…


    Companies Discussed: Cisco Systems, Inc. (CSCO), The Walt Disney Company (DIS), Spectrum Brands Holdings, Inc. (SPB), Maplebear Inc. (CART)

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    56 min
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