The Pragmatic Optimist

The Pragmatic Optimist

Here’s All Our Live Trades Since Launch

How Our Trades Have Fared So Far

Amrita Roy's avatar
Uttam Dey's avatar
Amrita Roy and Uttam Dey
Oct 09, 2025
∙ Paid
At The Pragmatic Optimist, we help hundreds of investors navigate the AI innovation landscape, identify businesses with strong growth trajectories and operational grit, and make long-term investments in the space with proven alpha generating returns. Winning calls: Celestica, Astera Labs, Credo, Micron, AppLovin, MongoDB and more

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A little over two weeks ago, we launched Live Trades to build our TPO Portfolio with $30,000 in initial capital that we plan to deploy in October, followed by monthly contributions of $10,000 as we expand our AUM.

Since then, we have now deployed close to 40% of our planned capital to the TPO Portfolio, which is currently returning over 6.2%. This is compared to the S&P 500’s 1.4% gain during this period of time.

The AI train is heating up, no doubt, but, at The Pragmatic Optimist, we believe in investing in companies with strong growth trajectories, operational grit, and robust balance sheets that are trading at an attractive risk-reward. This approach has allowed us to pick winners early in the cycle, with the average return of our “buy” ratings across companies in the AI ecosystem outperforming the S&P 500 by 3x since the time they were issued.

Note: When we publish a deep dive or a research note, we always provide our updated rating on the companies discussed with a price target and conviction score, which can be found in the AI Stock Rec Tracker

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Also, in case you have missed out, we sent out a post earlier this week where we updated our price targets, conviction scores, and ratings across companies in the semiconductor landscape, especially as the recent wave of dealmaking activity saw many of these stocks exceeding our previous price targets.

Our AI Stocks Have Updated Price Targets Now

Our AI Stocks Have Updated Price Targets Now

Uttam Dey and Amrita Roy
·
October 7, 2025
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In this post, we will provide a summary of the Live Trades executed so far, our rationale behind our allocation, and future plans of potentially increasing our position size. You can also see all of our Live Trades recorded in the AI Stock Rec Tracker.


Microsoft: A “Safe Haven” Amid Growing AI Bubble Concerns

Microsoft MSFT 0.00%↑ is currently our largest holding in the TPO Portfolio with a 10.4% allocation of part of a $30,000 portfolio. The stock currently has a Conviction Score of 10, with a PT of $620 per share, representing an upside of 18%+ from current levels.

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