When Rule Breakers Find Religion (or, at least profits)

8 snips

Nov 4, 2025

Guest

Jeff Santoro

Guest

Jason Hall

This week, analysts Jason Hall and Jeff Santoro dive into the transformation of major players in tech. Jason offers insight into Shopify’s strategy to compete against Amazon and the implications of AI-driven shopping. Jeff discusses Spotify's impressive margin improvements, weighing the risks of slower growth and user conversion challenges. They also explore Uber's remarkable shift to profitability and the implications of dynamic pricing practices. These 'reformed Rule Breakers' reveal how cash flow and discipline are becoming the new growth goals.

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INSIGHT

Shopify's Platform Scale Is Massive

Shopify built a sticky, do-it-yourself commerce platform that empowers merchants as an Amazon alternative.
Its GMV ($350B) highlights huge scale but comparing to Amazon's adjusted e-commerce revenue shows Shopify hasn’t surpassed Amazon overall.

INSIGHT

Growth Comes With Margin Pressure

Shopify grew revenue and GMV ~32% while spending to maintain its edge in marketing and R&D.
Rising merchant-related cost of revenue, however, is eroding gross margin and weighing on earnings growth.

ADVICE

Watch AI Partnerships Impacting Checkout

Monitor AI partnerships closely because they can reroute checkout flows and payment captures away from Shopify.
Do evaluate whether increased volume from agentic shopping offsets lost payment revenue per transaction.

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Spotify, Shopify, and Uber were once the poster children for “growth at any cost.” Today, they’re talking cash flow, margins, and discipline. In today’s episode of Motley Fool Money, host Emily Flippen is joined by analysts Jason Hall and Jeff Santoro to dig into what these “reformed Rule Breakers” are getting right - and where the risks still lurk.

They discuss third quarter earnings reports for:

- Shopify and how its business stacks up against Amazon and agentic shopping in the battle for online commerce.

- Spotify’s margin makeover, and how the business has created scale in an industry many were skeptical of

- Uber’s transformation from “broken IPO” to cash-flow machine, and how its pricing algorithm has unlocked margin potential

Companies discussed: SHOP, SPOT, UBER, GRAB

Host: Emily Flippen, Jason Hall, Jeff Santoro

Producer: Anand Chokkavelu

Engineer: Dan Boyd, Natasha Hall

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