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

E99 • Apr 6, 2023 • 32 mins

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.

Key Points

  • Matt McGinnis emphasizes the importance of velocity in business, stating that out-executing the competition is a key differentiator for success in a good market.
  • He advises founders to be willing to pivot or abandon a venture if it's not working, rather than persisting due to pride or loyalty to investors.
  • Matt highlights the benefits of pre-existing trust in business partnerships, as it allows for more open debate and efficient decision-making without fear of damaging the relationship.

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

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