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Why Entrepreneurs Should Rethink Everything with Damion Lupo, Ep. 26

Dec 28, 2017

Today’s episode of Just the Tips couldn’t come at a better time for many entrepreneurs. At a time of the year when we’re reevaluating our lives, what we’re doing, what we think we should be doing instead, it’s the perfect opportunity to listen to this interview with deep thinker and financial freedom advocate Damion Lupo. Damion opens up about his failures, how that set on a path to helping others, and how he goes about finding what’s truly important. He’s a pretty radical thinker, and Dean and I really got a lot out of this episode, and we think you will, too.

The key to success: failing fast

Right off the bat, Damion introduced us to his philosophy of “failing fast.” He says that often when we fail at something, we fail to learn and we keep repeating the same mistakes over and over again. But Damion switches that up by failing in order to learn, so he can then apply what he’s learned to his next step. And by knowing he’s going to fail fast, he says he’s able to move much more quickly, essentially baking the notion into his DNA and avoiding the trap of overanalysis that tends to slow down many entrepreneurs. Damion is a true original thinker, and if you ever feel like you’re stuck spinning your wheels, you need to hear what he has to say.=

Detach failure from your self-worth

Damion opened up about a time not too long ago when he started a company and raised $20 million in investments, and then lost all of that money. And what he says is fascinating: He took that experience and learned to detach it from his self-worth. He knew that companies fail, that investments aren’t guaranteed, and that he could learn from his mistakes and learn how to pivot much quicker next time, and so he went back out and raised a million dollars for a new company. And a lot of that shift came from not judging himself by whether he’s had good or bad results with his company. I think a lot of us could use this advice.

Rethink everything and worry about nothing

As Damion says, one of the ways you can release all of that toxicity that builds up in you after you’ve failed at something is to help others. So in 2012, he was rethinking and reevaluating what he was doing, and interrogating what values drove him to do what he does. And that’s what led him to write his first book, The Reinvented Life, and led me to ask him about what he sees as the spiritual side of wealth. As he says, money is a side effect. What you need to be doing is looking at what impact you can have on people, how you can help people, not on how much money you can make. It’s a really fascinating conversation and not one you’ll hear many entrepreneurs having.

How to build financial freedom

This is probably the most spiritually intense episode of Just the Tips. Damion is all about stripping down the unnecessary chaos in people’s lives, and figuring out what’s most important to them. And then from there, it’s about building the financial freedom so they can enjoy those important things. And as he says, it’s all about taking it one step at a time, not just hopping on a plane to Bali. Maybe it’s the time of year, but we think you’re really going to want to listen to and reflect on this week’s episode, and we’re so glad to have had Damion on.

Outline of This Episode

  • [3:22] Damion on failing fast
  • [7:23] An example of failing fast
  • [14:55] Damion’s philosophy on financial freedom
  • [17:42] The spiritual side of money
  • [20:52] The work Damion is doing right now
  • [25:09] What it’s like after you follow his process
  • [29:59] The value of the 12-week sprint

Resources & People Mentioned

Music for “Just The Tips” is titled, “Happy Happy Game Show” by Kevin MacLeod (http://incompetech.com) Licensed under Creative Commons: By Attribution 3.0 License

Connect With James and Dean

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