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The Neon Show
Hi, I am your host Siddhartha! I have been an entrepreneur from 2012-2017 building two products AddoDoc and Babygogo. After selling my company to SHEROES, I and my partner Nansi decided to start up again. But we felt unequipped in our skillset in 2018 to build a large company. We had known 0-1 journey from our startups but lacked the experience of building 1-10 journeys.
Hence was born the Neon Show (Earlier 100x Entrepreneur) to learn from founders and investors, the mindset to scale yourself and your company. This quest still keeps us excited even after 5 years and doing 200+ episodes.
We welcome you to our journey to understand what goes behind building a super successful company. Every episode is done with a very selfish motive, that I and Nansi should come out as a better entrepreneur and professional after absorbing the learnings.
The Neon Show
When Founders Should Quit Their Startups with Matt MacInnis | COO Rippling
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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
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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.
Subscribe for real founder stories, investor perspectives, economist breakdowns, and a behind-the-scenes look at how we’re doing it all at Neon.
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Check us out on:
Website: https://neon.fund/
Instagram: https://www.instagram.com/theneonshoww/
LinkedIn: https://www.linkedin.com/company/beneon/
Twitter: https://x.com/TheNeonShoww
Connect with Siddhartha on:
LinkedIn: https://www.linkedin.com/in/siddharthaahluwalia/
Twitter: https://x.com/siddharthaa7
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This video is for informational purposes only. The views expressed are those of the individuals quoted and do not constitute professional advice.