LU 371: How Working with the Right People Can Spark Innovation with Jim McKelvey (podcast)

Joining us on the show today is multifaceted, entrepreneur’s entrepreneur, Jim Mckelvey! Jim is currently developing his project, Invisibly, which aims to revolutionize the ways that consumers interact with advertising on media platforms. He is also the co-founder of Square and has started seven companies in total! His recent book, The Innovation Stack is compiled through his experience and research into what has allowed the most successful companies to create their own lane, and in it, he notes the common factors of the most innovative business in history. Jim explains how he learned the important skill of surrounding himself with more experienced and intelligent people and complimenting this with the ability to support and strengthen their work. We also get into the opportunity of calamity before discussing the need for humor and bravery in the life of an entrepreneur. For all this and a bunch more thought-provoking conversation, listen in with us today!


  • [00:21] Before we jump into today’s interview, please rate, review, and subscribe to the Leveling Up Podcast!
  • [01:24] Jim’s first book that he wrote during college and the skills he acquired during those years.
  • [02:23] How Jim met Jack Dorsey as a teenager.
  • [03:29] Jim’s role at Square and his attitude towards starting companies.
  • [05:11] The beginnings of starting a payment company and the moment that inspired it.
  • [06:16] The surprising growth of Square and its shaky path to success.
  • [08:05] The concept of the innovation stack and the motivations behind Jim’s book.
  • [10:56] The two types of problems in the world and what this means for solutions.
  • [12:55] Understanding the differences between businesspeople and entrepreneurs.
  • [15:16] The example of Southwest Airlines and its innovation stack.
  • [17:40] A better definition of disruption and ways to work in non-innovative spaces.
  • [19:19] Invisibly’s two main goals and their overarching mission statement.
  • [23:37] The way that Invisibly works for consumers online and in media.
  • [26:14] Business in the pandemic and the history of companies during a calamity.
  • [27:59] Why Douglas Adams’ books are so helpful for kindling the entrepreneurial spirit.
  • [29:27] The professional usefulness of saying ‘no’.
  • [30:05] Where Jim would invest a billion dollars currently.
  • [31:20] Jim’s departure from Square and his focus on family and projects he cares about.
  • [33:10] The need for more entrepreneurs and dispelling the hero myth.

Resources From The Interview:

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