Right Tail Capital founder Jeremy Kokemor is giving artificial intelligence a greater role in assessing the businesses held by the investment firm, as improving tools and wider adoption raise the stakes for companies’ competitive positions and earnings. He plans to scrutinize both firms whose advantages AI could weaken and businesses positioned to use the technology effectively, while cautioning that enthusiasm for AI does not make every related stock a sound investment.
Growing AI use changes Kokemor’s view
Kokemor said his first experience with ChatGPT left him intrigued but unconvinced of its practical value. The tool could produce answers that sounded plausible but were inaccurate. As the technology improved, he began using AI to edit text and expanded its role in investment research during 2025.
Earlier this year, he tried using Claude Cowork to build a family calendar tool that combined work and personal calendars with email, helping his family prepare for upcoming activities. The first version was useful, but it also ran into model failures, interrupted tasks and repeated permission requests.
More recently, Kokemor has used personal AI agents such as GrokBot and Muse more often in both work and daily life. Tasks like managing the family calendar have become easier and more effective, he said, as the systems have improved at interpreting intent and completing multi-step work rather than simply answering questions.
Seeing those capabilities advance has led Kokemor to view AI as potentially one of the most consequential technological shifts of his investing career—and perhaps his lifetime. He believes it could materially change the economics of individual companies.
Portfolio companies face both opportunity and pressure
Kokemor said many Right Tail Capital holdings continue to grow their earnings, and he expects them to keep creating value. AI’s prominence in the market does not, by itself, mean those companies have lost their existing competitive advantages. Still, some holdings are not seen as direct beneficiaries of AI and could face pressure as the technology develops.
He said recent stock-market performance has been driven to a significant extent by companies viewed as direct AI beneficiaries. Aside from Alphabet (GOOGL), Right Tail Capital has relatively limited direct exposure to that group. Kokemor also acknowledged that he had found himself hoping AI-related investments would underperform, a reaction he said did not fit with his increasingly positive assessment of the technology.
That shift does not mean chasing stocks labeled “AI winners.” Recent share-price strength is not, on its own, a reason to invest, he said, and strong demand for a technology does not guarantee attractive investment returns. A company can grow revenue rapidly yet deliver poor returns if it must commit too much capital to achieve that growth. Being right about a technology’s direction and being right about an investment are separate judgments.
Three areas of focus for portfolio reviews
As Kokemor assigns a higher likelihood to AI having a significant impact, he expects portfolio assessments to change in three ways. First, he will pay closer attention to companies whose core businesses could be weakened by AI, particularly where valuations may not fully reflect that risk.
Second, he is open to considering more companies with durable competitive positions that do not depend on betting on a particular technology or model. Third, he will look for businesses that can use AI to strengthen advantages they already have. In his view, long-term beneficiaries may include not only companies developing AI but also those that use it effectively.
The investment process itself will remain grounded in fundamental research, including analysis of competitive advantages, management, reinvestment opportunities, balance sheets, valuations and long-term earnings power. A company will not be sold simply because the market does not classify it as an AI beneficiary. But if AI changes its economics, Kokemor said, Right Tail Capital will revise its assessment accordingly.
The letter states that Right Tail Capital is registered as an investment adviser in Virginia and Louisiana. Portfolio performance cited in the letter is based on the adviser’s brokerage account, which has been invested since May 16, 2022, and has not been audited by a third party. Individual account results may differ based on investment start dates, cash flows, fees, taxes and trading costs.