

Constructing a Software Investing Thesis in the Age of AI with Ben Brostoff, Editor/Writer of the Stock Talk Newsletter
Jun 11, 2025
Ben Brostoff, a software engineer at Klaviyo and the mind behind the Stock Talk newsletter, shares his unique perspective on microcap investing. He reveals his strategy of targeting 8–10% returns while mitigating risks. Ben discusses how AI alters the evaluation of software companies and highlights the importance of thorough due diligence. His journey from investment banking to tech informs his insights on competitive advantages in the SaaS space. Listeners will appreciate his actionable frameworks and essential tips for navigating the complexities of investing in this dynamic sector.
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Episode notes
Ben's Unique Investing Journey
- Ben Brostoff transitioned from investment banking to software engineering and blogging about investing.
- He requires writing a blog post before owning any stock to maintain investment discipline.
Investment Return Philosophy
- Targeting an 8% to 10% return with minimal risk shapes Ben's investing philosophy.
- Microcaps require assuming higher upside scenarios to justify their increased risk.
AI Transforming Software Engineering
- AI is transformative in software engineering by accelerating coding and deployment.
- AI impacts software development efficiency but isn’t yet a full replacement for human skills.