I’ve been that guy. I’ve bought shares in what I thought were good companies and then just stopped looking. OK, maybe I looked. But when the stock went up, or down, I didn’t act. In some cases, I made money. In others, I lost money. What I know now is that investing is a constant balance between selecting good investments and managing your exposure to them.
Meet Samuel – Your Personal Investing Prophet
Double your CRWV exposure with Tradr's CWVXToday, I’d like to look at how three of TheStreet Pro’s experts manage their investments in real time.
A Superbowl Indicator You Should Pay Attention To
Doug Kass has featured in all four of the articles I’ve written for TipRanks, as well as the videos I’ve recorded with TipRanks’ Julie Gillespie on the TipRanks YouTube channel. That’s testimony to the value I get from reading his work. And this week’s article is a fun one. It’s about how watching the Super Bowl can make you a better investor.
I was a professional trader back in 2000 and remember the excitement around the Dotcom stocks. I can’t tell you who was in the Super Bowl that year, but I can tell you that the commercials were better than the on-field action. The Cat Herding commercial for EDS was classic. The Pets.com sock puppet sang a love song for animals that brought a tear to my eye. And E*Trade announced that they wasted $2 million on a dancing monkey.
In 2000, Doug Kass created the Super Bowl indicator as a contrary indicator. He looked at the money being spent and thought that those companies were either flush with cash and probably due to correct, or they were failing and making one last attempt to attract an audience. E*Trade corrected. Pets.com failed. Either way, it was the internet companies that spent heavily on Super Bowl ads in 2000, and the Nasdaq (NDX) proceeded to lose more than 70% before bottoming in 2003.
Think this was a one-time observance? Crypto exchange FTX spent heavily on ads in 2022 before filing for bankruptcy later that year. It’s not just a bearish indicator. Kass says that underrepresented industries are usually ripe for a rebound.
Last week, in “My Prescient Super Bowl Indicator Says These Stocks May Be Big Winners in 2026,” Kass gave us two sectors to consider on the upside and one surprise on the downside.
On the bullish side, automobile manufacturers and financial services companies bought fewer ads than expected. He thinks these sectors could outperform in 2026.
On the bearish side, 60% of the ads were related to consumer products. Staples companies have ripped higher in 2026, and Kass’s indicator says they may have gotten ahead of themselves.
As we discussed, Pepsi (PEP) was Kass’s stock of the year. He’s already sold it, having watched the stock top $170 per share, but with Apple (AAPL) replacing Pepsi as the Halftime show sponsor, he thinks Pepsi shares could continue to outpace Apple shares this year, too.
How does this impact your portfolio? Kass’s point is that this is a sentiment indicator. The decision to buy ads, or not, is based on how confident management is in their future earnings, and the companies dumping money on Super Bowl ads are often overconfident.
Next year, when you watch the Super Bowl, you can cheer for your favorite team and out-of-favor stocks, too!
Adding to a Winner in TheStreet Pro Portfolio
Chris Versace is the manager of TheStreet Pro’s Portfolio, which holds 33 stocks using a sort of growth at a reasonable price strategy. Chris is a smart guy who considers valuation as well as the drivers of a company’s earnings when selecting a stock.
Each holding in the portfolio is weighted to account for around 3% of the portfolio’s total value. When Chris really believes in an idea, he might overweight the stock to be about 4% of the portfolio. When the stock rises, he’ll trim it back, taking profits that can be allocated to other opportunities.
One holding that Versace has overweighted is SuRo Capital (SSSS). It’s a business development company, a way for investors like you and me to get in on early-stage venture-backed companies. You may have heard of two of their holdings: CoreWeave (CRWV), which has already gone public, and OpenAI, which is expected to IPO later this year.
Chris thinks the exposure to OpenAI is important and will drive shares of SuRo higher. In “We’re Stepping Up and Buying More Shares of This Holding,” he outlines the catalysts that make SuRo a bargain today.
- SuRo’s CRWV position should benefit from an increase in hyperscaler capital spending this year.
- SuRo exited holdings in 2025 that will provide the cash for the company’s upcoming dividend of over 2%.
- The company is due to revise its Net Asset Value, which should be significantly higher based on its ownership of OpenAI.
- The company holds other well-known tech companies like Canva and Plaid that are expected to IPO this year.
But it’s OpenAI that’s the big driver of SuRo lately, and Chris provides a great overview of OpenAI’s prospects leading up to its IPO in “OpenAI’s Continued Expansion of Its Revenue Stream Bodes Well for 4 Holdings.”
The big news is that OpenAI will start monetizing ChatGPT by selling ads. You probably saw Anthropic poke fun at them in a Super Bowl commercial on Sunday. It was my favorite commercial. Nevertheless, Versace thinks this will be big for OpenAI.
They’re also getting into the insurance business. The company just approved the first AI application for an insurance provider on ChatGPT, which Versace believes will drive future revenue back to the company.
AI has been the talk of the year, and Versace is adding to a portfolio holding in the space that’s paid off.
Managing Risk in a 2026 Stock Pick of the Year
In “TheStreet Pro: 3 “Left Behind” Stocks that Could Shoot to the Moon,” I talked about Stephen “Sarge” Guilfoyle’s amazing track record for selecting big winners for his stock pick of the year. 2026 hasn’t gotten off to a good start for Sarge’s pick, SoFi Technologies (SOFI). The stock is off around 20% year-to-date.
Sarge is not the kind of guy who buries his head in the sand when an investment goes against him. On the contrary. He has a rule that he looks to trim losses when a stock loses 8%. Now, he’s owned SOFI for some time and is up overall, but he’s been trading the position, too, in the hopes of making more money.
When the stock falls, he looks to manage risk. His plan was to use the 200-day Simple Moving Average as a line in the sand. Initially, he bought more shares when SOFI dropped to that level, around $23.
However, the stock continued to fall, and Sarge wrote last Wednesday that he was “Eyeing a SoFi Sale as My Stock of the Year Struggles.” The stock didn’t improve, and on Monday, Sarge said that he would be “Making the ‘Right Size’ Move with SoFi.”
Remember that Sarge has owned SoFi shares since they were far below the current price. So, he could have just held on. But he looked at his overall position and decided that he simply owned too much SOFI. So, he sold all the shares he bought recently, taking a loss.
The important thing is that he’ll live to trade another day. He believes in SoFi’s fundamental business case and will be looking for a new entry point. If the stock drops further, he’ll become even more excited about it. If it stabilizes here and begins to rally, he’ll bide his time and buy shares when he’s ready.
Either way Sarge is protecting his capital during a time when the stock has become unpredictable.
Summing It Up
Investing isn’t easy. To be a stock picker, you’ve got to find an edge. Perhaps that’s being creative with the data you look at. Like Doug Kass using the Super Bowl as an indicator. Or, averaging into a position that’s going your way, like Chris Versace in the Pro Portfolio. Or, and this is critical, perhaps it’s having a plan for how to take your losses when an investment goes against you.