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:
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Where to find Matt MacInnis:
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Where to find Brett Berson:
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Where to find First Round Capital:
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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
