TIVP105: Shopify (SHOP): The Big Winner of Agentic Commerce? w/ Shawn O'Malley & Daniel Mahncke

Shawn O’Malley and Daniel Mahncke revisit Shopify (NASDAQ: SHOP) fifteen months after Shawn pitched it, called it one of the best businesses they’d ever studied, and recommended passing on the stock at around $80 per share. Since then, the stock has nearly doubled, gross merchandise volume has grown more than 30% for five straight quarters, 2025 revenue rose 30% to over $11.5 billion, and Shopify paid off its convertible notes and launched its first-ever buyback program, now totaling $5 billion.

Shawn and Daniel grade their original analysis: what they got right about the business, what they got wrong about the numbers, and whether the decision-making process itself was flawed. They dig into how Shopify became central to agentic commerce through its Catalog of over a billion products, the Universal Commerce Protocol it co-developed with Google, and agentic storefronts inside ChatGPT, Gemini, and Copilot. They also cover Amazon blocking Meta’s Muse agent while Shopify partnered with it, the bear case that merchants will vibe-code their own stores, Sidekick’s rapid adoption, and whether a great business is worth owning at 112 times operating profits.

IN THIS EPISODE YOU’LL LEARN:

(00:00:00) Intro

(00:00:57) How to grade an investment decision without falling for hindsight bias

(00:07:05) What Shawn and Daniel got right and wrong when they passed on Shopify in 2025

(00:13:55) How Shopify sustained more than 30% GMV growth for five straight quarters

(00:15:10) Why Shopify merchants captured nearly half of all new U.S. e-commerce dollars

(00:24:55) Valuation discussion of Shopify

(00:33:43) What agentic commerce is and how Shopify’s Catalog and Universal Commerce Protocol power it

(00:50:52) Why AI shopping may favor independent brands over Amazon and Etsy

(01:01:57) Why merchants are unlikely to vibe-code their way off Shopify

(01:10:38) What Ben Graham’s P/E matrix says Shopify is worth today

(01:13:52) Whether Shawn and Daniel will add Shopify to the Intrinsic Value Portfolio

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

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