The Entrepreneurial Leap: Impacting 1,000,000 Entrepreneurs-in-the-Making (with Gino Wickman)

Gino Wickman is one of the most prolific and impactful thought leaders in the entrepreneurial space, teaching and inspiring countless people through his books, the Entrepreneurial Operating System® (EOS®), and now, Entrepreneurial Leap, a resource to help entrepreneurs-in-the-making get a huge jump-start.

Gino is also one of the most voracious learners I have ever encountered, but you wouldn’t have guessed if you met him in high school. He was lost, confused, and rebellious — he was mislabeled a troublemaker, but what he really needed was for someone to show him what else was possible outside of a typical 9-to-5.

That’s why Gino created Entrepreneurial Leap: to teach what he needed most, as Daniel Kennedy says. “It’s not like I had it all figured out and had this perfect plan, just the opposite,” Gino says. “I was terrified. I just knew that academics were not the way for me to learn the things that I wanted to learn and the things that I wanted to do in life.

“So, my passions, my teachings, the things that I’m obsessed about, they absolutely all stem from wounds and pain from the past. That is absolutely why I’m teaching that mislabeled derelict that I was back at 18, so that anybody out there that’s age 13 to 23 that’s kind of struggling with figuring all this out, this is a how-to manual if you think you’ve got this genetic encoding [to be an entrepreneur].”

Leap’s mission is to impact 1,000,000 entrepreneurs-in-the-making over the next 10 years. Think you might be one of them? Take Gino’s free Entrepreneur-in-the-Making Assessment to find out.

What Brett asks:

  • [02:33] Tell us about the beginning of your story.
  • [05:00] Tell me about living in nine cities by the age of 10.
  • [10:05] Why couldn’t you connect with school, instead choosing to be rebellious?
  • [19:28] How did your early jobs start to pull on the threads of your passion?
  • [30:50] Tell me about your experience in therapy and how your life and work evolved from the work you did in therapy.
  • [42:54] How did Landmark Forum serve your experience of transformation?
  • [51:05] How did Entrepreneurial Leap come to be?
  • [58:24] Can you speak to the role of mentorship?
  • [01:02:52] Can you explain more about your collaboration model?

Lessons for intentional living:

  • Gino says he’s never met anyone that didn’t need a little bit of therapy — and I haven’t either. This inner work of understanding who you are is a vital part of intentional living.
  • Let your freak flag fly — or, as Gino’s therapist put it, “fuck ‘em.” Just be yourself 100%, no holds barred. That doesn’t mean “screw everybody, I’m better than everyone else.” It means ignore other opinions and don’t let judgment get to you. Learn how to be vulnerable and authentic.
  • The negative connotation around “imposter syndrome” is nonsense. That’s just called being a human being, taking a risk, putting yourself out there, and getting good at something.