When Founders Should Quit Their Startups with Matt MacInnis COO Rippling

Matt MacInnis spent 6 years as COO at Rippling and now leads as CPO. He joined Rippling in 2019, when there were only 70 people, and has led the company across multiple stages. Before that, Matt was a founder for 9 years, building Inkling after 7 years at Apple. These three chapters of his career shape this conversation. We focus on how to build and operate teams as a company scales. Matt explains how he thinks about speed versus real progress, and which parts of building a company should move fast and which should move slowly. He shares how he decided when to introduce processes at Rippling, when to keep things informal, and how to recognize when a process that once helped the company had started to slow it down. We discuss how his role changed as Rippling grew from around 70 people to 100, then to 500, and now to thousands. He explains what he paid attention to at each stage and which metrics he deliberately did not obsess over. These are practical lessons for founders, from the earliest days of a startup to the challenges of scaling a large organization. 0:00 - Trailer 01:11 – One thing people get wrong about building a business? 04:01 – Great founders find markets that already exist 06:36 – What does a “death march” mean at Apple? 10:11 – How to build a good team in early-stage startup? 12:33 – Learnings from Apple to Inkling 18:11 – Processes to set up in startups 25:20 – Humans always optimize for comfort (and why that’s bad instinct) 33:09 – Why success teaches you more than failure 36:01 – How should processes change as company scales? 42:11 – How is AI changing the software industry? 54:03 – If Matt were starting up today, how would he do it? 57:07 – How would Next-gen PM roles look like? 01:01:51 – Matt shares about Rippling CEO Parker 01:04:32 – Founder instinct vs Data 01:06:06 – Over-optimizing for employee comfort 01:07:27 – If building a startup feels comfortable, it’s probably dead 01:08:36 – One thing only CEO’s should do forever 01:11:15 – One piece of startup advice Matt doesn’t trust ------------- India’s talent has built the world’s tech—now it’s time to lead it. This mission goes beyond startups. It’s about shifting the center of gravity in global tech to include the brilliance rising from India. What is Neon Fund? We invest in seed and early-stage founders from India and the diaspora building world-class Enterprise AI companies. We bring capital, conviction, and a community that’s done it before.

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When Founders Should Quit Their Startups with Matt MacInnis COO Rippling is an episode from 100x Entrepreneur by Siddhartha Ahluwalia.

This episode is 80:33 long.

This episode was published on Feb 7, 2026.

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