Guest: Matt MacInnis, COO of Rippling

One of the most important things a non-founder can do, says Rippling COO Matt MacInnis, is to learn how to operate in the context of the company they’re joining. His CEO, Parker Conrad, “spikes” in certain skill areas, and the rest of the executive team needs to maximize his ability to thrive while “taking care of the rest of it.” Matt likened the work to being a hobbyist airplane pilot, who can’t get a license without knowing all the minute details about their plane’s engine and aerodynamics.

“You can’t be a good pilot if you don’t understand the engine, because if something goes wrong, you want to be able to troubleshoot it,” he says. “An executive coming in to fly your airplane better learn the engine.”

Chapters:

(01:08) - Telling Rippling’s story
(04:27) - Founding & failing at Inkling
(09:30) - Different types of hard
(13:55) - Discipline and stamina
(15:22) - Meeting with Steve Jobs
(19:20) - Definitely, give up!
(22:29) - Product-market fit
(27:15) - Founders and culture
(33:24) - Executive instincts
(36:06) - Talent Signal and AI
(40:06) - 150 former founders
(44:08) - Zero to one projects
(48:06) - The failure of Silicon Valley Bank
(55:25) - Routines and discipline
(59:37) - Disagreeing with Parker
(01:02:25) - Who Rippling is hiring
(01:03:37) - What “grit” means to Matt

Mentioned in this episode: Parker Conrad, London Breed, Apple, Sequoia Capital, Sapphire Ventures, Tenaya Capital, digital textbooks on iPad, Oricom, Netscape, Peter Cho, Eddy Cue, John Couch, iBooks, Slack, Airbnb, Paul Graham, Brian Chesky, “founder mode,” Larry Ellison, Ivan Zhao and Notion, Intel and ARM, Salesforce, United Airlines, LLMs, GitHub, DocuCharm, Peter Thiel, Mamoon Hamid, Expensify, Navan, Costco, Comcast, HBO’s Silicon Valley, Jensen Huang and NVIDIA, and Taylor Swift.

Links:

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This episode was edited by Eric Johnson from LightningPod.fm

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