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.
—
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

—
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


—
Where to find Matt MacInnis:

LinkedIn: https://www.linkedin.com/in/macinnis/


Twitter/X: https://twitter.com/stanine


—
Where to find Brett Berson:

LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/


Twitter/X: https://twitter.com/brettberson


—
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


—
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