EP55: The Entrepreneur's Inner Journey

The Conscious Entrepreneur

“I love helping entrepreneurs shift into focusing on their ‘inner game,’ because then they get to both have a better experience—more joyful, less stressful, more enlivening, more playful—and more likely to succeed,” says Dave Kashen, a highly regarded leadership coach in Silicon Valley. He shares how embracing life as it unfolds, instead of clinging to rigid expectations, can help entrepreneurs tap into creativity and find peace, leading to more sustainable success.

In this episode, Dave talks with Alex Raymond about the “inner game” and conscious leadership. When entrepreneurs stop chasing external validation and focus on internal awareness, they can lead from a place of resilience and authenticity. Dave believes that by practicing presence, responsibility, and vulnerability, leaders can build stronger connections with their teams, which not only enhances personal fulfillment but also drives business success. Could this shift in perspective change the way you approach leadership?

Quotes

• “There are two primary games that people tend to play in life. One is, ‘Can I get life to match my mind’s idea of how life should be?’ The other is, ‘Can I just be with life as it is and relax my mind’s idea of how life should be?’ Most people are playing the first game and it’s a really challenging game. Even when you win, the joy, peace, and contentment don’t last very long. Because life is dynamic and our mind tends to be a bit more rigid, it’s really hard to get them to match.” (02:47 | Dave Kashen)
• “I realized at some point that the richer, more well-workable game—a game you could actually win—is the other game, where I can more and more relax my mind’s idea, or let go or disconnect from my mind’s idea of how things should be, so I can just be present with life as it is.” (03:31 | Dave Kashen)
• “The irony is that entrepreneurs are dreamers. So, we’re great at dreaming up some future, but then we collapse the desired future into the present, wishing we were already there, and just create suffering for ourselves and drain our energy.” (19:07 | Dave Kashen)
• “I believe the most successful entrepreneurs are the ones with the most conviction.” (45:58 | Dave Kashen)
• “I think a leader’s primary function is to serve… Leadership is the art of discernment. There’s never like a one way and one rule, but can you discern moment to moment what best serves—what best serves our vision, what best serves people? And I find the more you’re present, above the line, the clearer you are about what best serves.” (47:53 | Dave Kashen)

Links

Connect with Dave Kashen:

Website: https://www.davekashen.com/

Connect with Alex Raymond:

LinkedIn: https://www.linkedin.com/in/afraymond/

Website: https://consciousentrepreneur.us/

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