Constructing a Software Investing Thesis in the Age of AI with Ben Brostoff, Editor/Writer of the Stock Talk Newsletter

My guest on the show today is Ben Brostoff, software engineer at Klaviyo and the writer behind the Stock Talk newsletter on Substack. Ben has a fascinating perspective on investing—he started out in investment banking, taught himself to code, and now spends his free time researching microcap companies, especially in the software and tech space.

In this episode, we dive into Ben’s investing philosophy—why he targets 8–10% returns with the least amount of risk, how AI is changing the way he evaluates software moats, and why he won’t own a company unless he’s written a blog post about it. We also dig into some of the key lessons he’s learned, from the dangers of leverage to the power of doing more than just reading a 10-K.

Ben shares actionable frameworks for evaluating microcap software companies, offers a nuanced view on AI’s impact on infrastructure and margins, and explains why, for him, true due diligence means turning over every rock.

And for full disclosure, we discussed a number of companies during today’s podcast. I am not a shareholder in any of them.

For more information about the Stock Talk Newsletter, please visit: https://stocktalknewsletter.substack.com/ 

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