The Reality of Entrepreneurship: Matt MacInnis on Building Inkling, Exiting, and Scaling Rippling to an $11 Billion Valuation

The Dealroom with Shamus Madan

In this episode, Shamus Madan engages with Matt MacInnis, discussing his journey from founding Inkling to his transition to Rippling. They delve into the concept of Rippling as a compound startup, misconceptions about such startups, and how to manage growth in economic tightening. They also touch on ethical layoff management and insights for future founders.

Matt MacInnis began his career at Apple, spending seven years in the education and business development sector. After his time at Apple, he embarked on a new mission to build his own company, Inkling, a digital publishing platform for educational materials that raised over $102 million in funding and partnered with leading textbook publishers.

Now Matt is the Chief Operating Officer at Rippling, an all-in-one HR and IT platform that eliminates a lot of the administrative burden required to run a company. He joined when there were just 70 employees, and today they are ranked as one of LinkedIn’s top startups with over 1800 employees and valued at $11.25 Billion.

Twitter of Host (Shamus Madan): @mbitpodcast

Twitter of Guest (Matt MacInnis): @stanine

(0:00) Introduction and Matt MacInnis's career journey (4:25) Founding of Inkling - motivation, challenges, and success (7:50) Lessons from Inkling and transition to Rippling (14:30) Trust and shared experience in leadership (17:01) The unique strategy and concept of Rippling as a compound startup (22:21) Misconceptions and realities of compound startups (24:00) Growth and efficiency amidst economic tightening (27:32) Ethical layoff management and final thoughts for next-generation founders (29:35) Encouragement and insights on starting a company (31:57) Wrap up and closing remarks