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 episode artwork

EPISODE · Dec 13, 2025 · 55 MIN

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

from Smart Investing with Brent & Chase Wilsey · host Brent and Chase Wilsey

Another lawsuit against generative AI company Perplexity for copyright infringementThe 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 drainApple 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 portfolioYou 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 HarvestingWhile 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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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

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