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
