Introduction

Matt MacInnis is the COO at Rippling, an all-in-one HR, IT, and finance platform for businesses, which last raised $500M at a $11.25B valuation. Before Rippling, Matt was the co-founder and CEO at Inkling, a mobile learning platform that was acquired in 2018. He also held several management roles at Apple.

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In today’s episode, we discuss:

• Lessons on culture, org-design, and product from Rippling
• Characteristics of great CEOs
• How to a better executive leader
• Leading with kindness and impatience
• How to fight entropy

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Referenced:

• Andy Roddick: https://www.atptour.com/en/players/andy-roddick/r485/overview
• Apple: https://www.apple.com
• Bain & Company: https://www.bain.com/
• Bill Campbell: https://en.wikipedia.org/wiki/Bill_Campbell_(business_executive)
• Conscious Business: https://www.amazon.com.au/Conscious-Business-Build-Value-Through/dp/1622032020
• Google: https://www.google.com
• Inkling: https://www.inkling.com/
• McCaw Cellular: https://en.wikipedia.org/wiki/McCaw_Cellular_Communications
• McKinsey: https://www.mckinsey.com/
• Microsoft: https://www.microsoft.com
• Oracle: https://www.oracle.com
• Parker Conrad: https://www.linkedin.com/in/parkerconrad/
• Peter Currie: https://en.wikipedia.org/wiki/Peter_Currie_(businessman)
• Rippling: https://www.rippling.com
• The Effective Executive: https://www.amazon.com.au/Effective-Executive-Peter-Ferdinand-Drucker/dp/0060833459

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Where to find Matt MacInnis:

• LinkedIn: https://www.linkedin.com/in/macinnis/
• Twitter/X: https://twitter.com/stanine

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Where to find Brett Berson:

• LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
• Twitter/X: https://twitter.com/brettberson

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Where to find First Round Capital:

• Website: https://firstround.com/
• First Round Review: https://review.firstround.com/
• Twitter/X: https://twitter.com/firstround
• YouTube: https://www.youtube.com/@FirstRoundCapital
• This podcast on all platforms: https://review.firstround.com/podcast

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Timestamps:

(00:00) Introduction

(02:14) Great CEOs don’t worry about their weaknesses

(06:31) The third-time founder mindset

(08:09) Why every great CEO is impatient

(11:54) How executives fight entropy

(19:11) Experience ≠ wisdom

(21:26) Managing workplace politics

(24:02) Why all businesses should dogfood

(26:20) Overseeing employee expenses

(27:43) The best CEOs don’t need coaching

(29:55) The hidden cost of advice

(40:40) Why execs are “tortured but happy”

(44:16) Clear versus first principles thinking

(51:09) Finding first principles thinkers

(53:13) Why people overcomplicate culture

(55:53) Don’t make this mistake when interviewing

(59:26) The importance of anti-patterns

(61:27) Important business values

(63:28) How Matt thinks about output

(66:33) Rippling’s key leadership principle

(71:02) Why kindness matters

(72:03) Freeing yourself from self-doubt