Jim McKelvey is a serial entrepreneur, inventor, philanthropist, and artist.  He cofounded the mobile payments company Square and sits on the Board.  He also founded Invisibly, a digital content company, LaunchCode, a nonprofit that teaches technology literacy, and a glass art studio. His book is called The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time.

 

Some interesting insights from this episode:

  • He has never had a life plan and because of that, he’s become very comfortable with uncertainty.
  • He was a state debate champion and owed much of his success to the ability to read the judges and adjust his strategy accordingly.
  • “If you want to be successful and make some money, copy what works. But if you want to have a phenomenally successful company, you have to do something original.”
  • The big insight was rather than going after an existing market of merchants already using credit cards, Square decided to go after a market that didn’t even exist – the tiny mom and pop merchants without access to the credit card payment networks.
  • They designed a small card reader that looked really cool and got your attention but was flimsy and difficult to use. But the novelty of it turned every Square sale into a Square advertisement. This allowed the product to go viral without needing to spend one dollar on advertising.
  • What allowed Square to survive a competitive attack by Amazon and thrive as a standalone company was their innovation stack. An innovation stack is a series of innovations needed to provide a new product or service and that collectively work together to provide a competitive advantage in the marketplace.
  • Training as an artist was a big help in mentally preparing to be an entrepreneur.
  • “Excellence is something that’s above and beyond normal good. It’s something that’s surprisingly wonderful.”

 

Show Notes

Book: The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time

Non-profit: LaunchCode

New startup: Invisibly

Jerry Colonna is the founder and CEO of Reboot.IO, an executive coaching and leadership development firm whose coaches are committed to the notion that better humans make better leaders. Previously he was a successful venture capitalist with JPMorgan Partners and Flatiron Partners focused on technology startups. His new book is titled Reboot: Leadership and the Art of Growing Up.  He lives in Boulder, Colorado.

 

Some interesting insights from this episode:

  • Growing up in a chaotic environment with an alcoholic father and mentally ill mother drove his associating money with safety.
  • There was a dissonance between the way he felt internally and the way he was perceived in the world which led to a deep depression.
  • You can’t be a better leader without being a better human and you can’t be a better human without going through radical self-inquiry.
  • Radical self-inquiry is the process by which self-deception becomes so skillfully and compassionately exposed that no mask can hide us anymore.
  • We all have psychological baggage – our inner demons – which hold us back as leaders and we must confront those demons in order to grow.
  • It is a fallacy to think that leadership is all about having all the answers and not having any fear or any doubt. Authentic leadership is about accepting your imperfections.
  • Learn about the important difference between grit and stubbornness.
  • “We have to be willing to accept life as it is, not as we wish it might become. To live in the reality of what is today, not what might be in the future.”

 

Links:

Book: Reboot: Leadership and the Art of Growing Up

Reboot Website: www.reboot.io

Jerry Colonna Bio: www.reboot.io/team/jerry-colonna