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 12, 202555 MIN
Smart Investing with Brent & Chase Wilsey

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 12, 202555 MIN

Description

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 publisher and publishes it for people to read. The Times is also including infringements for use of its videos, podcasts and images. The Times said in the lawsuit they are seeking damages, which at this point is unknown and injunctive relief which includes removing all of the Times content from Perplexity’s products. This would be a major problem for Perplexity if they were to lose this case because the whole AI system pulls information from all across the web, and this would leave a big hole in the end result of Perplexity’s information. The Times is not the only publisher suing Perplexity, other lawsuits have been filed by Dow Jones and the New York Post. If one company were to win in court that would be a major problem for AI companies like Perplexity. First it would set a precedent and other publishers would likely sue, it could also lead to less accurate information as there would be less sources to pull data from.    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 has taken from Apple a top designer named Alan Dye. Also Jony Ive, who is a Steve Jobs protégé and helped build the iPhone along with the Apple Watch, is heading over to OpenAI to help Sam Altman. It’s not just the top people leaving though as apparently dozens of Apple engineers along with designers who are knowledgeable in audio, watch design, robotics, and much more are also finding a new home at OpenAI. Running a major technology company like Apple and striving for new innovation makes it difficult when a company is losing top management and star engineers and designers. I don’t think this will cause a major drop in the stock short term, but it could be difficult longer term for the company when it comes to innovation and new products, which could concern investors in the years to come!   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 discount considering there are down around 36% from their peak. History shows this could be a very good opportunity. There’s only been two times over the last roughly 50 years or so when commercial property prices were down more than 10%. You have to go back to the early 1990s, which was about 35 years ago, and who could forget the 2008 great recession. How should you invest in office buildings and commercial property? The best and the easiest way is to use public real estate investment trusts, which are known as REITs. Please do not let your broker sell you private real estate of any sort so they can get paid a big commission. REITs that trade on the market are commission free and completely liquid unlike private real estate deals. With public REITs you can many times receive good investment yields between 4% and 6%. However, make sure to understand the fundamentals to insurethat dividend yield is safe. A history lesson shows that commercial property under performed from 1997 to 2000 when the tech boom was happening, but when the tech boom ended and went bust, commercial real estate did very well. Could the same thing happen now as there are signs that the AI rally could end? If you do invest in a good quality public real estate investment trust, you should have at least a 4 to 5 year time horizon to hold that investment.   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 the same investment, they can immediately repurchase it, since wash-sale rules do not apply to gains. However, even though the gain itself is taxed at 0%, the added income may increase the taxation of Social Security benefits, pulling more of those benefits into taxable income. For those who don’t face that issue, gain harvesting resets their cost basis and reduces the taxes they will owe later if they sell in a higher-income year when their capital gains rate jumps to 15% or even 20%. This strategy can also make sense for those currently in the 15% capital gains bracket who expect to be pushed into the 20% bracket later. Overall, capital-gain harvesting can be a powerful tool in years of temporarily low income.   Companies Discussed: The Brink's Company (BCO), PVH Corp. (PVH), Pure Storage, Inc. (PSTG) & The Kroger Co. (KR)