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 5, 202555 MIN
Smart Investing with Brent & Chase Wilsey

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 5, 202555 MIN

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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 by railroads and automobiles during this revolution. The third industrial revolution came around the mid-1990s. Some of us who are 50 years or older may remember the effects. Electronics including personal computers, information technologies, and this scary thing called the World Wide Web were developed during this revolution. The fourth industrial revolution is happening now and it’s scary because we don’t know what the future holds. This revolution includes digital, physical, and biological technologies. This includes AI, the Internet of Things, and robotics as well. The reason this is scarier than the third revolution with personal computers was that people could see how they could benefit and get more done and maybe use that computer to start a web-based business. Currently with AI, people are not seeing how it will benefit or improve their lives but only how it could take away their livelihood by making their job obsolete. There could be a slowdown in the advancement of AI similar to what happened in the late 70s with nuclear power. People as a whole rejected nuclear power, and it has taken almost 50 years to be accepted as we can see in today’s newspapers. Based on history, it looks like the acceptance of AI may slow down because polls show that just 40% of people said the AI industry could be trusted to do the right thing, and 57% say the government needs more regulation on tech and AI. Maybe your job is safe for longer than you thought.   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 asset. The CEO, Michael Slayer, is saying if they must, they will sell Bitcoin to raise the cash to pay the dividends and interest payments. The convertible bonds could also be problematic down the road as they are due in about 4.4 years on average and come with a combined interest rate of 0.421%. The stock itself has been pulverized, and its market cap has been as low as $49 billion from a high of $128 billion in July. MSCI has proposed cutting digital asset treasury companies from its indexes if crypto tokens make up a major part of the assets. This decision will come in a little over a month on January 15th and if this happens, Strategy could see $2.8 billion in passive outflows. JPMorgan estimates that about $9 billion of the company's market cap is tied to passive and index ETFs and mutual funds. This could put more pressure on the stock if more indexes also decide to remove these treasury companies. You won’t believe how the company makes their profit and loss statement. When the price of Bitcoin rises, the company books a paper profit even if it did not sell any Bitcoin. Obviously, if Bitcoin goes down in value, they must book the losses as well. One must love the estimates for the earnings of Strategy for 2025.  Strategy is expected to report a loss of $5.5 billion or a profit of $6.3 billion or something in between. That is some great guidance! I don’t know where Bitcoin is going today, tomorrow or anytime in the future, but I would be sweating bullets if I held Bitcoin or Strategy in my clients’ portfolios or my portfolio!   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 saw strong online sales as they totaled $11.8 billion and grew by 9.1% year over year. A big question here is if the shopping was done to capitalize on deals in an attempt to save money. That could be an indicator of a weaker economy, but I don't believe that's the full story as shoppers told NRF at the end of Cyber Monday that they had about 53% of their holiday shopping remaining, which was similar to a year ago. For the full holiday season, the NRF expects record sales of between $1.1 trillion and $1.2 trillion from Nov. 1 through Dec. 31. This would be the first time sales would top $1 trillion, and it would represent a 3.7% to 4.2% increase from the year-ago holiday period.    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, especially retirees with lower taxable income, are already in the 0% long-term capital gains bracket, meaning losses may not even be needed; a married couple in retirement could have income near $150,000 and still realize long-term gains tax-free. Tax-loss harvesting can still be valuable when losses are large in percentage terms, when it helps avoid a higher tax bracket or IRMAA surcharges, when offsetting short-term gains (which long-term losses can do), or when exiting a position you don’t plan to repurchase.   Companies Discussed: Weyerhaeuser Company (WY), Netflix, Inc. (NFLX), Energizer Holdings, Inc. (ENR) & Valvoline Inc. (VVV)